Abstract
About 200 new naphthoquinones have been isolated in the last decade from plants, animals and micro-organisms, and whereas formerly sea urchins were the only marine source of these pigments they are now known to occur in hydroids, algae, sponges and marine fungi. o-Naphthoquinones continue to be of rare occurrence, outwith the sesquiterpenoid group, but meroterpenoid naphthoquinones are increasingly common. Pigments of particular interest are tectograndisone in which an anthraquinone unit is linked to a naphthoquinone, and the kinamycin group, formerly regarded as benzocarbazolequinones, which are now known to be derivatives of diazobenzofluorene.
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References
R.G. Binder, M.E. Benson and R.A. Flath, Phytochemistry, 1990, 28, 2799.
W.-U. Müller and E. Leistner, Phytochemistry, 1976, 15, 407;
W.-U. Müller and E. Leistner, Phytochemistry, 1978, 17, 1735.
X. Wang, J. Zhang, A. Cao et al., Zhongcaoyao, 1988, 19, 8 (Chem. Abs., 1988, 108, 183689).
L. Boisvert and P. Brassard, J. Org. Chem., 1988, 53, 4052.
N.G. Perry, J.W. Blunt and M.H.G. Munro, J. Nat. Prod., 1991, 54, 978.
L.W. Bieber, I. Messana, S.C.N. Lins et al., Phytochemistry, 1990, 29, 1955.
L.W. Bieber and M. Le Blanc, Acta Cryst., 1990, C46, 971.
A. Law, G. Thomas and D.R. Threlfall, Phytochemistry, 1973, 12, 1999.
A. Henry, R. Powls and J.F. Pennock, Biochem. J., 1987, 242, 367.
H. Ishii, J.-I. Kobayashi, H. Seki et al., Chem. Pharm. Bull., 1992, 40, 1358.
H. Ishii, J.-I. Kobayashi and T. Ishikawa, Tet. Lett., 1991, 32, 6907.
K. Ziegler, I. Maldener and W. Lockau, Z. Naturforsch., 1989, 44c, 468.
J.W. Suttie, Annu. Rev. Biochem., 1989, 54, 459;
J.W. Suttie, Biofactors, 1988, 1, 55.
S.W. Ham and P. Dowd, J. Am. Chem. Soc., 1990, 112, 1660;
P. Dowd, S.W. Ham and S.J. Geib, J. Am. Chem. Soc., 1991, 113, 7734;
P. Dowd, S.-W. Ham and R. Hershline, J. Am. Chem. Soc., 1992, 114,7613;
R.A. Flowers, S. Naganathan, P. Dowd et al., J. Am. Chem. Soc., 1993, 115, 9409.
R. Bentley, Microbiol Rev., 1982, 46, 241;
R. Bentley, Crit. Rev. Biochem. Mol. Biol., 1990, 25, 307;
P. Dowd, R. Hershline, S.W. Ham et al., Nat. Prod. Reps., 1994, 11, 251.
M. Akagawa-Matsushita, T. Itoh, Y. Katayama et al., J. Gen. Microbiol., 1992, 138, 2275.
M.D. Collins and F. Widdel, Syst. Appl. Microbiol., 1986, 8, 8.
A.F. Yassin, H. Brzezinka, K.P. Schaal et al., Zentralbl. Bakteriol Mikrobiol. Hyg. Ser. A, 1988, 267, 339;
R.M. Kroppenstedt and W. Mannheim, Int. J. Syst. Bacteriol., 1989, 39, 304.
B.J. Tindall and M.D. Collins, FEMS Microbiol. Lett., 1986, 37, 117.
M.D. Collins, R.M. Kroppenstedt, J. Tanoaka et al., Curr. Microbiol., 1988, 17, 275.
M.D. Collins, O.W. Howarth and J.J. Perry, FEMS Microbiol. Lett., 1986, 34, 167.
I. Takashi, F. Hiroshi, Y. Katayama-Fujimura et al., Biochim. Biophys. Acta, 1985, 840, 51.
M.D. Collins, FEMS Microbiol. Lett., 1985, 28, 21.
M.D. Collins, O.W. Howarth, E. Grund et al., FEMS Microbiol. Lett., 1987, 41, 35.
O.W. Howarth, E. Grund, R.M. Kroppenstedt and M.D. Collins, Biochem. Biophys. Res. Commun., 1986, 140, 916.
B.J. Tindall, V. Wray, R. Huber and M.D. Collins, Syst. Appl. Microbiol., 1991, 14, 218.
S. Thurl, I. Buhrow and W. Schäfer, Biol. Chem. Hoppe-Seyler, 1995, 366, 1079.
M.D. Collins and B.J. Tindall, FEMS Microbiol. Lett., 1986, 43, 307.
A. Rüttimann, Chimia, 1986, 40, 290.
M.D. Collins and F. Fernandez, FEMS Microbiol. Lett., 1985, 26, 181.
G.M. Carlone and F.A.L. Anet, J. Gen. Microbiol., 1983, 129, 3385.
M.D. Collins and F. Fernandez, FEMS Microbiol. Lett., 1984, 22, 273.
S.G. Batrakov, A.G. Panosyan, B.V. Rosynov et al., Biorg. Khim., 1976, 2,1538 (Chem. Abs., 1977, 86,52481).
M. Akagawa-Matsushita, Y. Itoh, Y. Katagama et al., J. Gen. Microbiol., 1992, 138, 2275.
M. Ishii, T. Kanasumi, Y. Igarashi et al., J. Bacteriol., 1987, 169, 2380.
K.C. Joshi, A.K. Sharma and P. Singh, Planta Med., 1986, 52, 71.
H. Nishihara, Y. Igarishi and T. Kodama, Arch. Microbiol., 1990, 153, 294.
A. Weische, M. Johanni and E. Leistner, Arch. Biochem. Biophys., 1987, 256, 212;
A. Weische, W. Garvert and E. Leistner, Arch. Biochem. Biophys., 1987, 256, 223.
M. Simantiras and E. Leistner, Phytochemistry, 1989, 28, 1381.
P.M. Dewick, Nat. Prod. Reps., 1989, 6, 263;
P.M. Dewick, Nat. Prod. Reps., 1991, 8, 149;
P.M. Dewick, Nat. Prod. Reps., 1992, 9, 153;
P.M. Dewick, Nat. Prod. Reps., 1993, 10, 233;
P.M. Dewick, Nat. Prod. Reps., 1994, 11, 173.
J.M. Heerding and H.W. Moore, J. Org. Chem., 1991, 56, 4048.
M. de Min, S. Croux, C. Tournaire et al., Tetrahedron, 1992, 48, 1869.
J. Koyama, T. Ogura, K. Tagahara et al., Phytochemistry, 1992, 31, 2907.
H. Itokawa, Y. Qiao and K. Takeya, Phytochemistry, 1991, 30, 637.
Y.-F. Qiao, K. Takeya, H. Itokawa et al., Chem. Pharm. Bull., 1990, 38, 2896.
H. Itokawa, Y. Qiao and K. Takeya, Phytochemistry, 1989, 28, 3465.
I.Y. Park, B.-K. Kim and Y.B. Kim, Arch. Pharm. Res., 1992, 15, 52 (Chem. Abs., 1992, 117, 208891).
A.K. Chauhan, M.P. Dobhal and P.N. Uniyal, Herba Pol., 1988, 34, 3 (Chem. Abs., 1989, 110, 209316).
T.-S. Wu, H.-J. Tien, M.-Y. Yeh et al., Phytochemistry, 1988, 27, 3787.
E. Ghera and Y. Ben-David, J. Org. Chem., 1985, 50, 3355.
A.C.F. Amaral and R.A. Barnes, J. Het. Chem., 1992, 29, 1457.
A.B. de Oliveira, D.S. Raslan and F. Khuong-Huu, Let. Lett., 1990, 31, 6873.
V.F. Ferreira, A.V. Pinto, M.C.F.R. Pinto et al., J. Chem. Res., 1987, 26.
O. Kodama, H. Ichikawa, T. Akatsuki et al., J. Nat. Prod., 1993, 56, 292.
P. Singh, R.T. Pardasani, A. Suri et al., Z. Naturforsch., 1992, 47b, 1031.
J. Mock, S.T. Murphy, E. Ritchie et al., Aust. J. Chem., 1979, 26, 1121.
S. Kuwuhara, A. Nemoto and A. Hiramatsu, Agric. Biol. Chem., 1991, 55, 2909.
S. Naganathan, R. Hershline, S.W. Ham and P. Dowd, J. Am. Chem. Soc., 1994, 116, 9831.
P.K. Sharma, R.B. Gupta, R.N. Khanna et al., Indian J. Chem., 1985, 24B, 1070.
P.K. Sharma, R.N. Khanna, B.K. Rohatgi et al., Phytochemistry, 1988, 27, 632.
R.B.N. Prasad and P.-G. Gülz, Phytochemistry, 1990, 29, 2097.
Y. Fujimoto, E. Yokoyama, T. Takahashi et al., Chem. Pharm. Bull., 1986, 34, 1497.
R. Barret and M. Daudon, Syn. Comm., 1990, 20, 2907.
G. Wurm and B. Gössler, Arch. Pharm., 1987, 320, 564.
M.P. Sibi, J.W. Dankwardt and V. Sniekus, J. Org. Chem., 1986, 51, 271.
K. Hirakawa, E. Ogiue, J. Motoyoshiya et al., Phytochemistry, 1986, 25, 1494.
G.S. Sidhu, M. Pardhasaradhi and M.H. Babu, Indian. J. Chem., 1975, 13, 749.
H. Harama, R. Faure, R. Elias et al., Phytochemistry, 1995, 39, 1483.
L.F. Fieser, and J.T. Dunn, J. Am. Chem. Soc., 1936, 58, 572.
G. Bringmann, Ch. Schneider and L.A. Assi, Planta Med., 1991, 57, Suppl. 2, A 10.
H. Möhle and H. Folttmann, Z. Naturforsch, 1987, 42b, 1181;
H. Möhle and H. Folttmann, Arch. Pharm., 1988, 321, 167.
J. Vijayalakshmi, S.S. Rajan and R. Srinivasan, Acta Cryst., 1987, C43, 2375.
G. Wurm and B. Goessler, Arch. Pharm., 1989, 322, 569.
H. Möhrle and H. Folttmann, Arch. Pharm., 1988, 321, 259.
T. Kamikawa and I. Kubo, Synthesis, 1986, 431.
N. Tamayo, A.M. Echavarren and M.C. Paredes, J. Org. Chem., 1991, 56, 6488;
E.M. Echavarren, N. Tamayo and D.J. Cardenas, J. Org. Chem., 1994, 59, 6075.
L. Boisvert and P. Brassard, J. Org. Chem., 1988, 53, 4052.
M. Watanabe, S. Hisamatsu, H. Hotokezaka et al., Chem. Pharm. Bull. 1986, 34, 2810.
L.S. Liebeskind, K.L. Granberg and J. Zhang, J. Org. Chem., 1992, 57, 4345.
M.H.H. Nkunya, J. Nat. Prod., 1985, 48, 999.
Zs. Rôzsa, I. Mester, J. Reisch et al., Planta Med., 1989, 55, 68.
J. Reisch and A. Bathe, Liebigs Ann. Chem., 1988, 543.
M. Higa, K. Himeno, S. Yogi et al., Chem. Pharm. Bull., 1987, 35, 4366.
B. Kreher, A. Neszmélyi and H. Wagner, Phytochemistry, 1990, 29, 605.
G.M.K.B. Gunaherath, A.A.L. Gunatilaka and R.H. Thomson, J. Chem. Soc. Perkin Trans. 1, 1988, 407.
F.M. Dean, P.G. Jones, R.B. Morton et al., J. Chem. Soc., 1963, 5336.
J.W. Mathieson and R.H. Thomson, J. Chem. Soc, (C), 1971, 153.
G.M.K.B. Gunaherath, A.A.L. Gunatilaka, P.J. Cox et al., Tet. Lett. 1988, 29, 719.
B.C. Maiti and O.C. Musgrave, J. Chem. Soc. Perkin Trans. 1, 1986, 675.
A.G. Brown, J.C. Lovie and R.H. Thomson, J. Chem. Soc., 1965, 2355.
A.V.B. Sankaram, V.V.N. Reddy and N. Marthandamurthi, Phytochemistry, 1986, 25, 2867.
T.J. Lillie, O.C. Musgrave and D. Skoyles, J. Chem. Soc Perkin Trans. 1, 1976, 2155.
T.J. Lillie and O.C. Musgrave, J. Chem. Soc Perkin Trans 1, 1977, 355.
A.V.B. Sankaram, V.V.N. Reddy and J.N. Shoolery, Indian J. Chem., 1987, 26b, 41.
S.M. Colegate, P.R. Dorling and C.R. Huxtable, Phytochemistry, 1987, 26, 979.
H.E. Harvey and J.M. Waring, J. Nat. Prod., 1987, 50, 767.
H. Laatsch, Z. Naturforsch., 1986, 41b, 377.
M.A. Rizzacasa and M.V. Sargent, Aust. J. Chem., 1988, 41, 1087.
L.T. Byrne, S.M. Colegate, P.R. Dorling et al., Aust. J. Chem., 1987, 40, 1315.
S.M. Colegate, P.R. Dorling, CR. Huxtable et al., Aust. J. Chem., 1985, 38, 1233.
J.-H. Wang, D.J. Humphreys, G.B.J. Stodulski et al., Phytochemistry, 1989, 28, 1825.
Z. Luo, D. Meksuriyen, C.A.J. Erdelmeier et al., J. Org. Chem., 1988, 53, 2183.
S.K. Sarkar and A. Bax, J. Magn. Res., 1985, 62, 109.
M.F. Comber and M.V. Sargent, J. Chem. Soc. Perkin Trans. 1, 1991, 2783.
Y. Kimiura, A. Shimada, H. Nakajima et al., Agric Biol. Chem., 1988, 52, 1253.
G. Weber, T. Hübner, A. Gierin et al., Z. Naturforsch., 1987, 42c, 1.
A.G. Mclnnes, J.A. Walter, J.L.C Wright et al., Can. J. Chem., 1990, 68, 1.
H. Lessmann, K. Krupa, H. Lackner et al., Z. Naturforsch., 1989, 44b, 353.
M.A. Brimble, E. Ireland and S.J. Phythian, Tet. Lett., 1991, 32, 6417;
M.A. Brimble and E. Ireland, J. Chem. Soc. Perkin Trans. 1, 1994, 3109.
R.G.F. Giles, P.R.K. Mitchell, G.H.P. Roos et al., J. Chem. Soc. Perkin Trans. 1, 1981, 2091.
K. Hamaguchi, T. Iwakeri, K. Imamura et al., J. Antibiot., 1987, 40, 717.
B. Botta, F. Delle Monache, G. Delle Monache et al., Tetrahedron, 1988, 44, 7193.
B. Botta, F. Delle Monache and G. Delle Monache, Tet. Lett., 1987, 28, 567.
F. Delle Monache, Rev. Latinoamer. Quim., 1985, 16, 5.
E. Fahy, R.J. Andersen, C Xu and J. Clardy, J. Org. Chem., 1986, 51, 5145.
E. Fahy, R.J. Andersen, G.D. Van Duyne and J. Clardy, J. Org. Chem. 1986, 51, 57.
E. Fahy and R.J. Andersen, Can. J. Chem., 1987, 65, 376.
E. Fahy, R.J. Andersen, H. Cunheng and J. Clardy, J. Org. Chem., 1985, 50, 1149.
J.S. Dahiya and S.R. Rimmer, Phytochemistry, 1988, 27, 3481.
H.C. Chen, Y.M. Lin, T.S. Shih et al., T’ai-wan K’o Hsueh, 1987, 41, 46 (Chem. Abs., 1989, 110, 151268).
T. Schoelly and I. Kapetanidis, Pharm. Acta Helv., 1989, 64, 66.
R. Caniato, R. Filippini and E.M. Cappelletti, Int. J. Crude Drugs Res., 1989, 27, 129.
G. Wurm and U. Geres, Arch. Pharm., 1990, 323, 319.
L.S. Liebeskind, Tetrahedron, 1989, 45, 3053.
B. Dinda and S. Saha, Chem. Ind., 1986, 823.
M.E. Botha, R.G.F. Giles and S.C. Yorke, J. Chem. Soc. Perkin Trans, 1, 1991, 85.
M.E. Botha, R.G.F. Giles, S.C. Yorke et al., S. Afr. J. Chem., 1991, 44, 84.
S.M. El-Sayyad, A.M. Abdel-Baky, E.Y. Backheet and K.W. Glombitza, Bull. Pharm. Sci. Assiut Univ., 1988, 11, 165 (Chem. Abs., 1990, 112, 83931).
W. Mammo, E. Dagne and W. Steglich, Phytochemistry, 1992, 31, 3577.
M. Garg, S.K. Garg and S.R. Gupta, Proc. Natl. Acad. Sci. India, Sect. A, 1985, 55, 95.
L. Kopanski, D. Karbach, G. Selbitschka and W. Steglich, Liebigs Ann. Chem., 1987, 793.
B.F.S. Prout, R.J. Hartman, E.P.-Y. Huang et al., Org. Synth. Coll. 1963, 4, 93.
B.-L. Wei, C.-N. Lin and S.-J. Won, J. Nat. Prod., 1992, 55, 967.
A.B. de Oliveira, D.T. Ferreira and D.S. Raslan, Tet. Lett., 1988, 29, 155.
A.B. de Oliveira, D.S. Raslan, M. do Carmo, M. Miraglia et al., Quim. Nova, 1990, 13, 302 (Chem. Abs., 1991, 115, 155037).
T. Matsumoto, A. Ichihara, M. Yamagiya et al., Helv. Chim. Acta, 1985, 68, 2324.
H. Itokawa, K. Matsumoto, H. Morita et al., Phytochemistry, 1992, 31, 1061.
W. Brade and A. Vasella, Helv. Chim. Acta, 1989, 72, 1649.
G.A. Poulton, G.W. Bushnell and Y.-L. Li, Can. J. Chem., 1992, 70, 2688.
M.A. Keniry and G.A. Poulton, Magn. Res. Chem., 1991, 29, 46.
M. Watanabe, M. Date and S. Furukawa, Chem. Pharm. Bull., 1989, 37, 292.
L.A. Decosterd, I.C. Parsons, K.R. Gustafson et al., J. Am. Chem. Soc., 1993, 115, 6673.
P.J. Fisher, A.E. Anson, J. Webster et al., Trans. Br. Mycol. Soc., 1988, 90, 499.
S.B. Singh, M.G. Cordingley, R.G. Ball et al., Tet. Lett., 1991, 32, 5279.
G.K. Poch and J.B. Gloer, Tet. Lett., 1989, 30, 3483.
K. Ohta, F. Kasahara, T. Ishimaru et al., J. Antibiot., 1987, 40, 1239.
H. Laatsch, Liebigs Ann. Chem., 1986, 1669.
H. Laatsch, Angew. Chem. Int. Ed. Engl., 1994, 33, 422.
C. Volkmann, E. Roessner, M. Metzler, Liebigs. Ann. Chem., 1995, 1169.
M. de Rosa, S. de Rosa, A. Gambacorta et al., Phytochemistry, 1977, 16, 1961.
Y. Ikeda, N. Ishida, C. Fukaya et al., Chem. Pharm. Bull., 1991, 39, 2351.
S. Fu and P. Xiao, Zhongcaoyao, 1986, 17, 434 (Chem. Abs., 1987, 106, 55728).
K. Inoue, M. Akaji and H. Inouye, Chem. Pharm. Bull., 1985, 33, 3993.
A.M. Moiseenkov, N.N. Balaneva, V.L. Novikov and G.E. Elyakov, Dokl. Akad. Nauk. SSSR, 1987, 295, 614;
V.L. Novikov, N.N. Balaneeva, A.M. Moiseenkov, Bull. Russ. Acad. Sci., 1992, 41, 1485.
Y. Tanoue, A. Terada and Y. Sugyo, J. Org. Chem., 1987, 52, 1437.
M. Braun and C. Bauer, Liebigs Ann. Chem., 1991, 1157.
M. Braun and R. Devant, Tet. Lett., 1984, 25, 5031;
M. Braun and R. Devant, Chem. Ber., 1988, 121, 397.
U. Eilert and B. Wolters, Plant Cell Tiss. Organ. Cult., 1989, 18, 1;
A.J. Parr, J. Biotechnol., 1989, 10, 1.
H. Inouye, S. Ueda, S. Inoue et al., Phytochemistry, 1979, 18, 1301.
K. Yazaki, H. Fukui and M. Tabata, Chem. Pharm. Bull., 1986, 34, 2290.
L. Heide and M. Tabata, Phytochemistry, 1987, 26, 1645, 1651.
L. Heide, H.G. Floss and M. Tabata, Phytochemistry, 1989, 28, 2643.
Y. Fujihata, Y. Hara, T. Ogino et al., Plant. Cell. Rep., 1981, 1, 59;
K. Yazaki, H. Fukui, M. Kikuma et al., Plant Cell Rep., 1987, 6, 131;
M. Tabata, H. Mizukami, N. Hiraoka et al., Phytochemistry, 1974, 13, 927;
H. Fukui, N. Yoshikawa and M. Tabata, Phytochemistry, 1983, 22, 2451;
L. Heide, N. Nishioka, H. Fukui et al., Phytochemistry 1989, 28, 1873;
M. Tani, H. Fukui, M. Shimomura et al., Phytochemistry 1992, 31, 2719.
A.S. Mellidis and V.P. Papageorgion, J. Nat. Prod., 1987, 50, 618.
M. Afzal and G. Al-Oriqat, Agric Biol. Chem., 1986, 50, 759.
G. Honda, F. Sakakibara, K. Yazaki et al., J. Nat. Prod., 1988, 51, 152.
R.K. Khajuria and S.M. Jain, Indian J. Chem., 1993, 32B, 390.
C.C. Chen, H.-J. Yu, J.C Ou et al., J. Chin. Chem. Soc., 1994, 41, 195 (Chem. Abs., 1994, 120, 319387).
O. Potterat, H. Stockli-Evans, J.D. Msonthi and K. Hostettmann, Helv. Chim. Acta, 1987, 70, 1551.
T. Ogasawara, K. Chiba and M. Tada, Phytochemistry, 1993, 33, 1095.
D.S. Fukuda, J.S. Mynderse, P.J. Baker et al., J. Antibiot., 1990, 43, 623.
T. Henkel and A. Zeeck, J. Antibiot., 1991, 44, 665.
K. Shiomi, H. Nakamura, H. Iinuma et al., J. Antibiot., 1986, 39, 494.
S. Imai, K. Fujioka, K. Furihata et al., J. Antibiot., 1993, 46, 1323.
G.K. Poch, J.B. Gloer and C.A. Shearer, J. Nat. Prod., 1992, 55, 1093.
R.E. Moore, H. Singh, C.W.J. Chang and P.J. Scheuer, Tetrahedron 1967, 23, 3271.
B. Caron and P. Brassard, Tetrahedron, 1991, 47, 4287.
A. Kobayashi, S. Yata, T. Hino et al., Agric. Biol. Chem., 1987, 51, 2857.
J.W. Westley, C-M. Liu, J.F. Blount et al., J. Antibiot., 1993, 46, 280.
N.N. Gerber and B. Wieclawek, J. Org. Chem., 1966, 31, 1497.
K. Shinya, S. Imai, K. Furihata et al., J. Antibiot., 1990, 43, 444.
K. Shinya, A. Shimazu, Y. Hayakawa and H. Seto, J. Antibiot., 1992, 45, 124.
K. Shin-ya, K. Furihata, Y. Hayakawa et al., Tet. Lett., 1990, 31, 6025.
U. Sankawa, H. Shimada, T. Sato et al., Tet. Lett., 1977, 483;
H. Seto and H. Yonehara, Tet. Lett., 1977, 487.
S. Funayama, S. Eda, K. Komiyama et al., J. Org. Chem., 1990, 55, 1132.
A. Horeau, Tet. Lett., 1961, 506.
C.J.W. Brooks and J.D. Gilbert. J. Chem. Soc. Chem. Commun., 1973, 194.
P. Wessels, A. Göhrt, A. Zeeck et al., J. Antibiot., 1991, 44, 1013.
G.J. Buist, C.A. Bunton and W.C.P. Hipperson, J. Chem. Soc. (B), 1971, 2128
S.J. Angyal and R.J. Young, J. Am. Chem. Soc., 1959, 81, 5251.
J.A. Cifonelli and F. Smith, Anal. Chem., 1954, 26, 1132.
C Pathirana, P.R. Jensen and W. Fenical, Tet. Lett., 1994, 33, 7663.
M. Pardhasaradhi and B.N. Rao, Phytochemistry, 1990, 29, 2355.
M. Pardhasaradhi, B. Krishnakumari and B.N. Rao, Indian J. Chem. 1991, 30B, 786.
A.C. Baillie and R.H. Thomson, J. Chem. Soc. (C), 1966, 2184.
J.H. Tatum, R.A. Baker and R.E. Berry, Phytochemistry, 1985, 24, 3019.
J.H. Tatum, R.A. Baker and R.E. Berry, Phytochemistry, 1987, 26, 795.
D. Parisot, M. Devys and M. Barbier, Phytochemistry, 1988, 27, 3002.
G.P. Arsenault, Tetrahedron, 1968, 24, 4745.
A.G. Medentsev and V.K. Akimenko, Phytochemistry, 1992, 31, 77.
D. Parisot, M. Devys and M. Barbier, Microbios. Lett., 1987, 36, 129.
K. Koike, K. Ishi, M. Mitsunaga et al., Chem. Pharm. Bull., 1991, 39, 939.
D. Bergeron, B. Caron and P. Brassard, J. Org. Chem., 1993, 58, 509.
K. Inoue, C.-C. Chen and H. Inouye et al., J. Chem. Soc. Perkin Trans. 1, 1981, 2764.
F.M. Hauser, P. Hewawasam and V.M. Baghdanov, J. Org. Chem., 1988, 53, 223.
C.B. de Koning, R.G.F. Giles, L.M. Engelhardt et al., J. Chem. Soc. Perkin Trans. 1, 1988, 3209.
A. Bekaart, J. Andrieux and M. Plat, Tet. Lett., 1992, 33, 2805.
V.H. Deshpande, R.A. Khan and N.R. Ayyangar, Syn. Comm., 1993, 23, 2677.
D. Molho, Bull. Soc. Chim. Fr., 1961, 1417.
N. Katagiri, J. Nakano and T. Kato, J. Chem. Soc. Perkin Trans. 1, 1981, 2710.
M.A. Rizzacasa and M.V. Sargent, J. Chem. Soc. Perkin Trans. 1, 1987, 2017.
K. Masuda, S. Funayama, K. Komiyama et al., J. Nat. Prod., 1987, 50, 418.
K. Matsuda, S. Funayama, K. Komiyama et al., J. Nat. Prod., 1987, 50, 958.
H.A. Anderson, J. Smith and R.H. Thomson, J. Chem. Soc., 1965, 2141;
R.E. Moore and P.J. Scheuer, J. Org. Chem., 1966, 31, 3272.
D.C. Sutton, F.T. Gillan and M. Susic, Phytochemistry, 1985, 24, 2877.
S.C Hooker and A. Steyermark, J. Am. Chem. Soc., 1936, 58, 1202.
J.W. Mathieson and R.H. Thomson, J. Chem. Soc. (C), 1971, 153.
R. Hout and P. Brassard, Can. J. Chem., 1974, 52, 88.
H. Inouye, H. Matumura, M. Kawasaki et al., Phytochemistry, 1981, 20, 1701.
A.M. Vidal-Tessier, P. Delaveau, B. Champion et al., Ann. Pharm. Fr., 1988, 46, 55.
C.L. Zani, A.B. de Oliveira and G.G. de Oliveira, Phytochemistry, 1991, 30, 2379.
M. Girard, D. Kindack, B.A. Dawson et al., J. Nat. Prod., 1988, 51, 1023.
Y. Fujimoto, T. Eguchi, C. Murasaki et al., J. Chem. Soc. Perkin Trans. 1, 1991, 2323.
V.F. Ferreira, A.V. Pinto, M.C.F.R. Pinto et al., Syn. Comm., 1989, 19, 1061.
C.C. Lopes, R.S.C. Lopes, A.V. Pinto et al., J. Het. Chem., 1984, 21, 621.
M.R. Meselhy, S. Kadota, K. Tsubono et al., Tetrahedron, 1994, 50, 3081.
L. David, J.-C. Gayet and H. Veschambre, Agric. Biol. Chem., 1985, 49, 2693.
J. Yue, Z. Lin, D. Wang et al., Phytochemistry, 1994, 35, 1023.
R.E. Moore, H. Singh and P.J. Scheuer, J. Org. Chem., 1966, 31, 3645.
M. Couturier and P. Brassard, Synthesis, 1994, 703.
C.C. Chen and M.H. Lee, Hua Hsueh, 1986, 44, 61 (Chem. Abs., 1986, 105, 168912).
N. Wu, H. Chen and Z. Wang, Zhongcaoyao, 1994, 25, 10 (Chem. Abs., 1994, 121, 5179).
M.C. Chang, I. Jimenez, M. Piovana et al., Bol. Soc. Chil. Quim., 1993, 38, 187 (Chem. Abs., 1994, 121, 5173).
H. Laatsch, Liebigs Ann. Chem., 1983, 299.
H. Laatsch, B. Renneberg, E. Duverney et al., Z. Naturforsch., 1995, 50b, 151.
C. Abeygunawardena, V. Kumar, D.S. Marshall et al., Phytochemistry, 1991, 30, 941.
C. Rivalle, E. Bisagni and J. Andre-Louisfert, Tetrahedron, 1974, 30, 3193.
H. Wagner, B. Kreher, H. Lotter et al., Helv. Chim. Acta, 1989, 72, 659.
C.C. Chen, Hua Hsueh, 1983, 41, 9 (Chem. Abs., 1984, 101, 207595).
CE. Heltzel, A.A.L. Gunatilaka, T.E. Glass et al., J. Nat. Prod., 1993, 56, 1500.
Y. Fujimoto, T. Eguchi, C. Murasaki et al., J. Chem. Soc. Perkin Trans. 1, 1991, 2323.
M. Girard, D. Kindack, B.A. Dawson et al., J. Nat. Prod., 1988, 51, 1023.
S. Ueda, T. Umemura, K. Dohguchi et al., Phytochemistry, 1994, 36, 323.
H. Koga, Y. Sakai, Y. Ohashi et al., Acta Cryst., 1991, C47, 1127.
K. Inoue, H. Inouye and C.-C. Chen, Phytochemistry, 1981, 20, 2271.
M.M. Rao and D.G.I. Kingston, J. Nat. Prod., 1982, 45, 600.
CL. Zani, A.B. de Oliveira and V. Sniekus, Tet. Lett., 1987, 28, 6561.
M. Watanabe and V. Sniekus, J. Am. Chem. Soc., 1980, 102, 1457.
P.R.R. Costa, S.C. Lopes, R.S.C Lopes et al., Syn. Comm., 1988, 18, 1723;
C.C Lopes, E.L.S. Lima, A.J. Monteiro et al., Syn. Comm., 1988, 18, 1731.
V. Guay and P. Brassard, J. Nat. Prod., 1986, 49, 122.
W.A. Ayer, M. Kamada and Y.-T. Ma, Can. J. Chem., 1989, 67, 2089.
P. Torres, R. Chinchilla, M.C. Asensi et al., Phytochemistry, 1989, 28, 3093.
O.B. Maximov, R.P. Gorshkova, L.S. Stepanenko et al., Khim. Prirod. Soedin., 1990, 400 (Chem. Abs., 1991, 114, 78633).
T. Bruun and A. Lamvik, Acta Chem. Scand., 1971, 25, 483.
K. Koniyama, S. Funayama, Y. Anraku et al., J. Antibiot., 1990, 43, 247.
M. Ishibashi, S. Funayama, Y. Anraku et al., J. Antibiot., 1991, 44, 390.
P. Adriaenssens, A.E. Anson, M.J. Begley et al., J. Chem. Soc. Perkin Trans. 1, 1994, 2007.
L. Carey, J.M. Clough and G. Pattenden, J. Chem. Soc. Perkin Trans. 1, 1983, 3005.
P.G. Dormer, A.B. Smith and S. Funayama, Tet. Lett., 1992, 33, 1717.
S. Funayama, M. Ishibashi, K. Komiyama and S. Õmura, J. Org. Chem. 1990, 55, 1132.
J.A. Dale, D.L. Dull and H.S. Mosher, J. Org. Chem., 1969, 34, 2543;
J.A. Dale and H.S. Mosher, J. Am. Chem. Soc., 1973, 95, 512.
R. Arhart and J.C. Martin, J. Am. Chem. Soc., 1972, 94, 5003.
P. Sedmera, S. Pospisil and J. Novak, J. Nat Prod., 1991, 54, 870.
J.H. Tatum, R.A. Baker and R.E. Berry, Phytochemistry, 1987, 26, 2499.
M. Devys, M. Barbier and S. Parisot, Heterocycles, 1990, 31, 1485.
A. Ali, R.W. Read and S. Sotheeswaran, Phytochemistry, 1994, 35, 1029.
S.R. Jammula, S.B. Pepalla, H. Telikepalli et al., Phytochemistry, 1991, 30, 2427.
R.E. Moore and P.J. Scheuer, J. Org. Chem., 1966, 31, 3272.
C.-M. Chen, Z.-T. Chen and Y.-L. Hong, Phytochemistry, 1990, 29, 980.
M. Wang and W. Liu, Phytochemistry, 1987, 26, 578.
J.S. Calderon and R.H. Thomson, J. Chem. Soc. Perkin Trans. 1, 1988, 583.
G.M. Strunz, C.-M. Yu and A. Salonius, Phytochemistry, 1989, 28, 2861.
D. Murali and G.S.K. Rao, Indian J. Chem., 1987, 26B, 668.
W.M. Best and D. Wege, Aust J. Chem., 1986, 39, 647.
M.S. Kemp and R.S. Burden, Phytochemistry, 1986, 25, 1261.
R.M. Letcher and I.M. Shirley, Phytochemistry, 1992, 31, 4171.
R.M. Letcher, K.-K. Cheung and I.M. Shirley, J. Chem. Res. (S), 1988, 271; J. Chem. Res. (M), 1988, 2001.
R.M. Letcher and M.-C. Wong, J. Chem. Soc. Perkin Trans. 1, 1992, 3035.
T.P. Veluchamy, D.M. Murali and G.S.K. Rao, Indian J. Chem., 1986, 25, 1247.
P.G. Forster, E.L. Ghisalberti, P.R. Jefferies et al., Phytochemistry, 1986, 25, 1377.
E.L. Ghisalberti, J. Ghosh and P.R. Jefferies, see ref. 279.
R.D. Stipanovic, H.L. Kim, D.W. Altman et al., Phytochemistry, 1994, 36, 953.
M.O.F. Goulart, A.E.G. Sant’ana and V. Horak, Mikrochim. Acta (Wien), 1986, 1, 23.
N.E. Mahoney and B.G. Chan, J. Nat. Prod., 1988, 51, 374.
M.A. Ferreira, T.J. King, S. Ali et al., J. Chem. Soc. Perkin Trans. 1, 1980, 249.
S. Abdo, M. de Bernardi, G. Marinomi et al., Phytochemistry, 1992, 31, 3937.
K. Kobayashi, H. Shimizu, A. Sasaki et al., J. Org. Chem., 1991, 56, 3204.
E. Ghera, R. Maurya and Y. Ben-David, Tet. Lett., 1986, 27, 3935.
W.G. Salmond, M.A. Barta and J.L. Havens, J. Org. Chem., 1978, 43, 2057.
P. Capdevielle and M. Maumy, Tet. Lett., 1983, 24, 5611.
T. Hayashi, F.T. Smith and K.-H. Lee, J. Med. Chem., 1987, 30, 2005.
L. Hari, L.F. de Buyck and H.L. de Pooter, Phytochemistry, 1991, 30, 1726.
D. Parisot, M. Devys and M. Barbier, J. Antibiot., 1992, 45, 1799.
D. Parisot, M. Devys and M. Barbier, J. Antibiot., 1991, 44,103.
D. Parisot, M. Devys and M. Barbier, Microbios, 1990, 64, 31.
I. Kurobane, N. Zaita and A. Fukuda, J. Antibiot., 1986, 39, 205.
I. Kurobane, L.C. Vining, A.G. Mclnnes et al., Can. J. Chem., 1978, 56, 1593.
J.H. Tatum, R.A. Baker and R.E. Berry, Phytochemistry, 1989, 28, 283.
D. Parisot, M. Devys and M. Barbier, Phytochemistry, 1989, 28, 3240.
K.V. Rao, K. Sreeramulu and D. Gunasekar, J. Nat. Prod., 1993, 56, 2041.
M. Barbier, M. Devys and D. Parisot, Syn. Comm., 1993, 23, 651.
J. Koyama, T. Ogura and K. Tagahara, Phytochemistry, 1994, 35, 1147.
A.B. de Oliveira, D.S. Raslan, G.G. de Oliveira et al., Phytochemistry, 1993, 34, 1409.
P.J. Houghton, R. Pandey and J.E. Hawkes, Phytochemistry, 1994, 35, 1602.
J. Yue, Z. Lin, D. Wang et al., Phytochemistry, 1994, 35, 1023.
C. Ito, T. Ono, E. Tanaka et al., Chem. Pharm. Bull., 1993, 41, 205.
D.A. Rama, D.S. Iyengar and M. Pardhasaradhi, Tetrahedron, 1994, 50, 2543.
H. Lessmann, J. Krupa, H. Lackner et al., Z. Naturforsch., 1993, 48b, 672.
S. Gupta, M. Ali and M.S. Alam, Phytochemistry, 1993, 33, 723.
G. Alemayehu, B. Abegaz, G. Snatzke et al., Phytochemistry, 1993, 32, 1273.
J. Li and M. Lin, Zhongcaoyao 1993, 24, 115 (Chem. Abs., 1993, 119, 91252).
O. Kazuhito, J. Zhao, M. Higa et al., Bull Coll. Sci. Univ. Ryukyus, 1992, 54, 17 (Chem. Abs., 1993, 118, 230163).
C.E. Heltzel, A.A.L. Gunatilaka, T.E. Glass and D.G.I. Kingston, Tetrahedron, 1993, 49, 6757.
K.H. Lee and H.W. Moore, Tet. Lett., 1993, 34, 235.
G. Sartori, F. Bigi, G. Coffred; et al., J. Chem. Res. (S), 1993, 324.
M. Aso and K. Kanematsu, Chem. Pharm. Bull., 1993, 41, 1549.
T. Kagamizono, A. Kawashima, K. Akira et al., Biosci. Biotechnol. Biochem., 1993, 57, 766.
D.W. Cameron, I.T. Crosby, G.I. Feutrill et al., Aust. J. Chem., 1992, 45, 2003.
L.A. Mitscher, S.R. Gollapudi, D.S. Oburn et al., Phytochemistry, 1985, 24, 1681.
J.E. McMurry and J. Melton, J. Org. Chem., 1973, 38, 4367.
D.W. Cameron, I.T. Crosby and G.I. Feutrill, Aust. J. Chem., 1992, 45, 2025.
M. Blouin, M-C. Bélande and P. Brassard, J. Org. Chem., 1990, 55, 1466.
S.B. Pepalla, S.R. Jammula, K.V.J. Rao et al., Phytochemistry, 1992, 31, 2103.
X.F. Wang, W.J. Lu, J.Y. Chen et al., Yaoxue Xuebao, 1993, 28, 122 (Chem. Abs., 1993, 119, 91204).
S.B. Jammula, S.B. Pepalla, H. Telikepalli et al., Phytochemistry, 1991, 30, 3741.
W. Mammo, Ph.D. Thesis, University of Addis Ababa, 1989.
D. Bergeron and P. Brassard, Heterocycles, 1992, 34, 1835.
R. Barret and M. Daudon, Syn. Comm., 1990, 20, 2907;
R. Barret and M. Daudon, Tet. Lett., 1990, 31, 4871.
C.B. de Koning, R.G.F. Giles and LR. Green, J. Chem. Soc. Perkin Trans. 1, 1991, 2743.
R.H. Thomson, in: The Total Synthesis of Natural Products (J. Apsimon, ed.), vol. 8, p. 311, Wiley, New York, 1992. Y. Naruta and K. Maruyama, in: The Chemistry of the Quinonoid Compounds (S. Patai and Z. Rappoport, eds.), Wiley, New York, 1988, 2 (pt. 1), 241.
E. Yoshii and T. Kometani, J. Syn. Org. Chem. Jap., 1986, 44, 918.
T. Hanumiah, D.S. Marshall, B.K. Rao et al., Phytochemistry, 1985, 24, 2373.
M.F. Semmelhack, J.J. Bozell, L. Keller et al., Tetrahedron, 1985, 41, 5803.
H. Uno, J. Org. Chem., 1986, 51, 350.
G.A. Kraus, M.T. Molina and J.A. Walling, J. Org. Chem., 1987, 52, 1273.
O.H.W. Decker and H.W. Moore, J. Org. Chem., 1987, 52, 1174.
L.D. Foland, O.H.W. Decker and H.W. Moore, J. Am. Chem. Soc., 1989, 111, 989.
G.A. Kraus, J. Shi and D. Reynolds, J. Org. Chem., 1990, 55, 1105.
G.A. Kraus, J. Li, S. Gordon et al., J. Am. Chem. Soc., 1993, 115, 5859.
M.A. Brimble and S.M. Lynds, J. Chem. Soc. Perkin Trans. 1, 1994, 493.
K. Shindo and H. Kawai, J. Antibiot., 1992, 45, 584.
O. Potterat, H. Zähner, C. Volkmann and A. Zeeck, J. Antibiot., 1993, 46, 346.
K. Tsuzuki, Y. Iwai, S. Õmura et al., J. Antibiot., 1986, 39, 1343.
T. Kumazawa, E. Oshima, H. Obase et al., JP 61152669, 1986 (Chem. Abs., 1987, 106, 17030).
H. Imai, K. Suzuki, S. Kadota et al., J. Antibiot., 1989, 42, 1186.
H. Tsujibo, T. Sakamoto, K. Miyamoto et al., Chem. Pharm. Bull., 1990, 38, 2299.
M.A. Brimble and J.A. Spicer, Aust. J. Chem., 1991, 44, 197.
K. Tatsuta, K. Akimoto, M. Annaka et al., J. Antibiot., 1985, 38, 680.
K. Tatsuta, K. Akimoto, M. Annaka et al., Bull. Chem. Soc. Jpn., 1985, 58, 1699.
D.W. Cameron, I.T. Crosby and G.I. Feutrill, Tet. Lett., 1992, 33, 2855.
M. Yamaguchi, S. Nakamura and T. Minami, Tet. Lett., 1990, 31, 3913.
S. Kakinuma, H. Ikeda, S. Õmura et al., J. Antibiot., 1990, 43, 391.
R. Curci, M. Fiorentino, L. Troisi et al., J. Org. Chem., 1980, 45, 4758.
S.P. Cole, B.A.M. Rudd, D.A. Hopwood et al., J. Antibiot., 1987, 40, 340.
M. Yamaguchi, S. Nakamura, T. Okuma et al., Tet. Lett., 1990, 31, 3913.
S. Kakinuma, H. Ikeda, S. Õmura and D.A. Hopwood, J. Antibiot., 1990, 43, 391;
S. Kakinuma, H. Ikeda and S. Õmura, Tetrahedron, 1991, 47, 6059.
J. Tsuji, M. Nisar and I. Shimizu, J. Org. Chem., 1985, 50, 3416.
D. Ling, L.S. Shield and K.L. Rinehart, J. Antibiot., 1986, 39, 345.
W.L. Russell, R.C. Pandey, C.P. Schaffner et al., J. Antibiot., 1988, 41, 149.
R.A. Nelson, J.A. Pope, R.C. Pandey et al., J. Antibiot., 1988, 41, 1659.
J.E. Hochlowski, G.M. Brill, W.W. Andres et al., J. Antibiot., 1987, 40, 401.
LP. Karwowski, M. Jackson, R.J. Theriault et al., J. Antibiot. 1988, 41, 1205.
M.A. Brimble and S.J. Phythian, Tet. Lett., 1993, 34, 5813.
N. Tanaka, T. Okabe, F. Isono et al., J. Antibiot., 1985, 38, 1327;
T. Okabe, K. Nomoto, H. Funabashi et al., J. Antibiot., 1985, 38, 1333.
T. Okabe, K. Nomoto and N. Tanaka, J. Antibiot., 1986, 39, 1.
S. Takano, K. Hasuda, A. Ito et al., J. Antibiot., 1987, 29, 765.
N. Tanaka, T. Okabe, F. Isono et al., J. Antibiot., 1985, 38, 1327.
A. Nakagawa, N. Fukamachi, K. Yamaki et al., J. Antibiot., 1987, 40, 1075.
H. Inouye and E. Leistner, in: The Chemistry of the Quinonoid Compounds (eds. S. Patai and Z. Rappoport), vol. 2 (pt. 2), 1293, Wiley, New York, 1988;
D. O.’ Hagan Nat. Prod. Reps., 1993, 10, 593 and earlier reviews in that series; see also D. O’Hagan, The Polyketide Metabolites, Horwood, Chichester, 1991 and E. Haslam, Shikimic Acid: Metabolism and Metabolites, Wiley, Chichester, 1993.
K. Tatsuta, H. Ozeki, M. Yamaguchi et al., Tet. Lett., 1990, 31, 5495.
K. Takeda, I. Sawada, A. Suzuki et al., Tet. Lett., 1983, 24, 4451.
K. Tatsuta, H. Ozeki, M. Yamaguchi et al., J. Antibiot., 1991, 44, 901.
D.A. Hopwood, F. Malpartida, H.M. Kieser et al., Nature, 1985, 314, 642.
S. Õmura, H. Ikeda, F. Malpartida et al., Antimicrob. Agents Chemother., 1986, 29, 13.
M.G. Patel, V. Hegde, A. Horan et al., J. Antibiot., 1989, 42, 1063.
V.R. Hegde, A.H. King, M.G. Patel et al., Tet. Lett., 1987, 28, 4485.
K. Nomura, K. Okazaki, K. Hori et al., J. Am. Chem. Soc., 1989, 109, 3403.
K. Okazaki, K. Nomura and E. Yoshii, J. Chem. Soc. Chem. Commun., 1989, 354.
Y. Takeuchi, M. Sudani and E. Yoshii, J. Org. Chem., 1982, 48, 4151;
E. Yoshii, Y. Takeuchi, K. Nomura et al., Chem. Pharm. Bull., 1984, 32, 4767.
T. Wakamatsu, H. Hara and Y. Ban, J. Org. Chem., 1989, 50, 108.
CE. Snipes, C.-j. Chang and H.G. Floss, J. Am. Chem. Soc., 1979, 101, 701;
A. Arnone, L. Camarda, R. Cardillo et al., Helv. Chim. Acta, 1979, 62, 30.
X.-g. He, C.-c. Chang, C.-j. Chang et al., Z. Naturforsch., 1986, 41c, 215.
C. Kitao, H. Tanaka, S. Minami and S. Õmura, J. Antibiot., 1980, 33, 711.
B. Krone, A. Zeeck and H.G. Floss, J. Org. Chem., 1982, 47, 4721.
B. Krone and A. Zeeck, Liebigs Ann. Chem., 1987, 751.
P.D. Singh, J.J. Johnson, C.A. Aklonis et al., J. Antibiot., 1985, 38, 706.
A. Zeeck, P. Russ, H. Laatsch et al., Chem. Ber., 1979, 112, 957.
J. Yang, S. Fan, H. Pei et al., J. Antibiot., 1991, 44, 1277.
Y. Hayakawa and Y. Toda, JP 90 60596, 1990 (Chem. Abs., 1990, 113, 113855).
K.M. Biswas and H. Mallik, J. Indian Chem. Soc., 1986, 53, 448.
V. Friese, A. Boos, H.-J. Bauch and E. Leistner, Phytochemistry, 1993, 32, 613.
Pers. comm. from F. Arcamone to E. Leistner, see Ref. 390.
F. Arcamone, W. Barbieri, G. Franchesci et al., J. Am. Chem. Soc., 1973, 95, 2008;
F. Arcamone, G. Franchesci, B. Gioia et al., J. Am. Chem. Soc., 1973, 95, 2009.
W.-L. Shieh and C.-N. Lin, Phytochemistry, 1992, 31, 364.
C.-N. Lin, W.-L. Shieh and T.-T. Jong, Phytochemistry, 1992, 31, 2563.
Y. Hano, R. Inami and T. Nomura, Heterocycles, 1993, 35, 1341.
S.L. Otten and J.P. Rosazza, J. Nat. Prod., 1981, 44, 562.
M. Gill and M.J. Kiefel, Aust. J. Chem., 1994, 47, 1967.
M. Gill and D.A. Lally, Phytochemistry, 1985, 24, 1351.
B. Steffan and W. Steglich, Angew. Chem. Int. Ed. Engl., 1984, 23, 445.
W. Steglich, H.-T. Huppertz and B. Steffan, Angew. Chem. Int. Ed. Engl., 1985, 24, 711.
M. Gill and W. Steglich, Prog. Chem. Org. Nat. Prods., 1987, 51, 1.
e.g. R.D. Bach and R.C Klix, Tet. Lett., 1986, 27, 1983;
M.A. Ciufolini and M.E. Browne, Tet. Lett., 1987, 28, 171;
M. Toyota and S. Terashima, Tet. Lett., 1989, 30, 829;
B. Pandey, U.R. Khire and N.R. Ayyangar, J. Chem. Soc. Chem. Commun., 1990, 1791;
LS. Aidhan and N.S. Narasimhan, Indian J. Chem., 1993, 32B, 222.
e.g. Y. Kita, R. Okunaka, T. Honda et al., Chem. Pharm. Bull., 1991, 39, 2106;
D.L. Boger and M. Zhang, J. Org. Chem., 1992, 57, 3974.
T.R. Kelly, N. Ohashi, R.J. Armstrong-Chong et al., J. Am. Chem. Soc., 1986, 108, 7100;
T.R. Kelly, S.H. Bell, N. Ohashi et al., J. Am. Chem. Soc., 1988, 110, 6471.
D.L.J. Clive, Y. Tao, A. Khodabocus et al., J. Chem. Soc Chem. Commun., 1992, 1489;
D.L.J. Clive, Y. Tao, A. Khodabocus et al., J. Am. Chem. Soc., 1994, 116, 11275.
L. Saint-Jalmes, C. Lila, J.Z. Xu et al., Bull. Soc. Chim. Fr., 1993, 130, 447.
A.V.R. Rao, A.K. Singh, B.V. Rao et al., Tet. Lett., 1993, 34, 2665;
A.V.R. Rao, Heterocycles, 1994, 37, 1893.
K. Nozaki, K. Oshima and K. Utimoto, J. Am. Chem. Soc., 1987, 109, 2547;
K. Nozaki, K. Oshima and K. Utimoto, Tet. Lett., 1988, 29, 6125.
J.-i. Shimada, K. Hashimoto, B.H. Kim et al., J. Am. Chem. Soc., 1984, 106, 1759.
D.J. Burnell and Y.-J. Wu, Can. J. Chem., 1990, 68, 804.
M. Gill and J. Yu, Nat. Prod. Lett., 1994, 5, 211.
S.F. Mason, R.H. Seal and D.R. Roberts, Tetrahedron, 1974, 30, 1671.
H. Nakamura, J. Kobayashi, M. Kobayashi et al., Chem. Lett., 1985, 713.
F.J. Schmitz and S.J. Bloor, J. Org. Chem., 1988, 53, 3922.
J. Kobayashi, T. Hirase, H. Shigemori et al., J. Nat. Prod., 1992, 55, 994.
N. Harada, T. Sugioka, H. Uda et al., J. Org. Chem., 1990, 55, 3158.
K. Kanematsu, S. Soejima and G. Wang, Tet. Lett., 1991, 32, 4761.
Y. Yamaguchi, K. Hayakawa and K. Kanematsu, J. Chem. Soc. Chem. Commun., 1987, 515.
M. Kobayashi, N. Shimizu, Y. Kyogoku et al., Chem. Pharm. Bull., 1985, 33, 1305.
M. Kobayashi, N. Shimizu, I. Kitagawa et al., Tet. Lett., 1985, 26, 3833.
N. Harada, T. Sugioka, Y. Ando et al., J. Am. Chem. Soc., 1988, 110, 8483.
N. Harada, H. Uda, M. Kobayashi et al., J. Am. Chem. Soc., 1989, 111, 5668.
K.A. Alvi, J. Rodriguez, M.C Diaz et al., J. Org. Chem., 1993, 58, 4871.
B. Dinda and G. Chel, Phytochemistry, 1992, 31, 3652.
T. Kagamizono, A. Kawashima, Y. Kishimura et al., Biosci. Biotechnol. Biochem., 1993, 57, 766.
For a review see E. Yoshii and T. Kometani, J. Syn. Org. Chem. Jap. 1986, 44, 918.
A.L. Elson, S.J. Box and M.L. Gilpin, J. Antibiot., 1988, 41, 570.
M.L. Gilpin, S.J. Box and A.L. Elson, J. Antibiot., 1988, 41, 512.
K. Nomoto, T. Okabe, H. Susuki et al., J. Antibiot., 1988, 41, 1124.
J. Krupa, H. Lessmann and H. Lackner, Liebigs Ann. Chem., 1989, 699.
C.P. Gorst-Allman, B.A.M. Rudd, C.-J. Chang and H.G. Floss, J. Org. Chem., 1981, 46, 455.
S. Kuwahara, N. Awai, M. Konno et al., J. Nat. Prod., 1996, in press.
M. Higa, Chem. Pharm. Bull., 1988, 36, 3234.
J. Krupa, H. Lackner, P.G. Jones et al., Z. Naturforsch., 1989, 44b, 345;
H. Lessmann, J. Krupa, H. Lackner et al., Z. Naturforsch., 1989, 44b, 353.
L.F. Fieser and J.L. Hartwell, J. Am. Chem. Soc., 1935, 57, 1482.
S.J. Gould, B. Shen and Y.G. Whittle, J. Am. Chem. Soc., 1989, 111, 7932.
Y. Kawasaki, Y. Goda and K. Yoshihara, Chem. Pharm. Bull., 1992, 40, 1504.
P. Singh, S. Jani and S. Bhargava, Phytochemistry, 1989, 28, 1258.
G. Wurm and U. Geres, Arch. Pharm., 1989, 317, 606.
R.P. Gupta and R.W. Franck, Synlett, 1990, 355.
M. Vairamani, B.N. Rao and M. Pardhasaradhi, Org. Mass Spectrom. 1991, 26, 33.
S.B. Claudio, J.A. Valderrama, R. Tapia et al., Syn. Comm., 1992, 22, 955.
R. Tapia, J.A. Valderrama and C. Quintanar, Heterocycles, 1994, 38, 1797.
Y. Iwai, K. Kimura, Y. Takahashi et al., J. Antibiot., 1983, 36, 1268.
K. Tsuzuki, Y. Iwai and S. Õmura, J. Antibiot., 1986, 39, 1343.
U. Himmelreich, S. Huneck, G.B. Feige et al., Z. Naturforsch., 1994, 49b, 1289.
K. Krohn, A. Michel, U. Flörke et al., Liebigs Ann. Chem., 1994, 1099.
K. Krohn, A. Michel, U. Flörke et al., Liebigs Ann.Chem., 1994, 1093.
R. Thiergardt, P. Hug, G. Rihs et al., Tet. Lett., 1994, 35, 1043.
S.B. Singh, D.L. Zink, J.M. Liesch et al., 1994, 59, 6296.
M. Maruyama, C. Nishida, Y. Takahashi et al., J. Antibiot., 1994, 47, 952.
K.M. Byrne, B.D. Hilton, R.J. White et al., Biochemistry, 1985, 24, 478.
R. McDaniel, S. Ebert-Khosla, D.A. Hopwood et al., J. Am. Chem. Soc., 1994, 116, 10855 and references therein.
M.C. Cone, P.J. Seaton, K.A. Halley and S.J. Gould, J. Antibiot., 1989, 42, 179;
P.J. Seaton and S.J. Gould, J. Antibiot., 1989, 42, 189.
K. Isshiki, T. Sawa, H. Naganawa et al., J. Antibiot., 1989, 42, 467.
T.A. Smitka, R. Bonjouklian, T.J. Perun et al., J. Antibiot., 1992, 45, 581.
J.-J. Young, S.-N. Ho, W.-M. Ju et al., J. Antibiot., 1994, 47, 681.
S. Õmura, A. Nakagawa, H. Yamada et al., Chem. Pharm. Bull., 1973, 21, 931.
G.I. Dmitrienko, K.E. Nielsen, C. Steingart et al., Tet. Lett., 1990,31, 3681;
G. Weeratunga, G.K.B. Prasad, J. Dilley et al., Tet. Lett., 1990, 31, 5713.
S. Mithani, G. Weeratunga, N.J. Taylor and G.I. Dmitrienko, J. Am. Chem. Soc., 1994, 116, 2209.
A.M. Echavarren, N. Tamayo and M.C. Paredes, Tet. Lett., 1993, 34, 4713.
S.J. Gould, N. Tamayo, C.R. Melville et al., J. Am. Chem. Soc., 1994, 116, 2207.
A. Furusaki, M. Matsui, T. Watanabe et al., Israel J. Chem., 1972, 10, 173.
P.J. Seaton and S.J. Gould, J. Am. Chem. Soc., 1987, 109, 5282.
M.C. Cone, CR. Melville, M.P. Gore and S.J. Gould, J. Org. Chem., 1993, 58, 1058.
K. Shin-ya, K. Furihata, Y. Teshima et al., Tet. Lett., 1992, 33, 7025.
C Volkmann, Diss., University of Göttingen, 1993.
H.-J. Knölker and N. O’Sullivan, Tet. Lett., 1994, 35, 1695.
T.-S. Wu, M.-J. Liou, C.-J. Lee et al., Tet. Lett., 1989, 30, 6649.
D. O’Hagan, S.V. Rogers, G.R. Duffin and R.L. Edwards, Tet. Lett, 1992, 33, 5585.
I. Casser, Diss., University of Bonn, 1986.
J.A. Wendt, P.J. Gauvreau and R.D. Bach, J. Am. Chem. Soc., 1994, 116, 9921.
W.S. Johnson, J.D. Bass and K.L. Williamson, Tetrahedron, 1963, 19, 861.
M.P. Winters, M. Stranberg and H.W. Moore, J. Org. Chem., 1994, 59, 7572.
J.-R. Dai, L.A. Decosterd, K.R. Gustafson, et al., J. Nat. Prod. 1994, 57, 1511.
J.F. Fisher and H. Nordby, Tetrahedron, 1966, 22, 1489.
K. Kosuge, K. Mitsunaga, K. Koike et al., Chem. Pharm. Bull., 1994, 42, 1669.
H.-P. Fiedler, A. Kulik and T.C. Schuez, J. Antibiol., 1994, 47, 1116.
M. Maruyama, C. Nishida, Y. Takahashi et al., J. Antibiol., 1994, 47, 952.
G. Alemayehu, B. Abegaz, G. Snatzke et al., Phytochemistry, 1992, 32, 1273.
A.M. Aquinaldo, O.P.M. Ocampo, B.F. Bowden et al., Phytochemistry, 1993, 33, 933.
R.D. Stipanovic and M.H. Wheeler, Pestic. Biochem. Physiol., 1980, 13, 198.
M.H. Wheeler and R.D. Stipanovic, Exp. Mycol., 1979, 3, 340.
A.G. Medentsov, B.P. Baskunov and V.K. Akimenko, Biokhimiya, 1989, 54, 619 (Chem. Abs., 1989, 111, 325).
H.-P. Fiedler, A. Kulik, T.C. Schuez et al., J. Antibiol., 1994, 47, 1116.
G. Helmchen, Tet. Lett., 1974, 1527.
Y. Hayakawa, K. Ishigami, K. Shin-ya and H. Seto, J. Antibiol., 1994, 47, 1344.
N. Harada, T. Sugioka, H. Uda et al., J. Org. Chem., 1994, 59, 6606.
W. Steglich, Pure. Appl. Chem., 1989, 61, 281.
D.S. Rycroft, J.D. Conolly, S. Huneck et al., Z. Naturforsch, 1995, 50b, 1557.
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Thomson, R.H. (1997). Naphthoquinones. In: Naturally Occurring Quinones IV. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-1551-0_2
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