Abstract
The title adduct was converted into 1,2-epoxymyrcene; its cationic 5-exo-cyclization gave a (±)-hop ether having the iridane-type skeleton. Effective syntheses of a furanoterpene perillene and some functionalized cyclopentanoid monoterpenes regioisomeric to iridoids were elaborated using sulfur-containing geraniol derivatives easily accessible from the same adduct in a synthetic sequence including the Pummerer reaction and anionic cyclization.
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References
A.M.Moiseenkov, V.V.Veselovsky, Z.G.Makarova, and V.M.Zhulin,Izv.Akad.Nauk SSSR. Ser.Khim., 1987, 1143 [Bull.Acad.Sci. USSR. Div.Chem.Sci., 1987, 1057].
A.M.Moiseenkov, K.V.Lebedeva, and B.A.Czeskis.Uspekhi Khimii, 1984,53, 1709 [Russian Chem.Rev.].
M.Miyazava and H.Kameoka,Agric.Biol.Chem., 1979,43, 2199; R.Ros and A.P.Bruins,Planta Med., 1980,38, 79.
A.M.Moiseenkov, V.A.Dragan, and V.V.Veselovsky,Uspekhi Khimii, 1991,60, 1225 [Russian Chem.Rev., 1991,60, 643].
T.Nishio and Y.Omote,J.Chem.Soc. Perkin Trans I, 1979, 1703; H.Nishyama, M.Sasaki, and K.Itoh,Chem.Lett., 1981, 1363.
O.P.Vig, O.P.Chugh, V.K.Handa, and A.K.Vig,J.Indian Chem.Soc., 1975,52, 199; B.A.Czeskis, P.Baekström, A.M.Moiseenkov, and T.Norin,Izv.Akad.Nauk SSSR. Ser.Khim., 1989,144 [Bull.Acad.Sci. USSR. Div.Chem.Sci., 1989,38, 131].
G.L.Olson, H.-C.Cheung, K.D.Morgan, C.Neukom, and G.Saucy,J.Org.Chem., 1976,41, 3287.
E.V.Polunin, I.M.Zaks, A.M.Moiseenkov, and A.V.Semenovskii,Izv.Akad.Nauk SSSR. Ser.Khim., 1979, 641 [Bull. Acad.Sci. USSR. Div. Chem. Sci., 1979,28, 594].
C.D.Broaddus,Acc.Chem.Res., 1968,1, 231.
D.A.Evans and G.C.Andrews,Acc.Chem.Res., 1974,7, 147.
D.G.Farum, T.Veysoglu, A.M.Carde, B.Duhl-Emswiler, T.A.Pancoast, and T.J.Reitz,Tetrahedron Lett., 1977, 4009.
K.Mori,Agric.Biol.Chem., 1974,38, 2045; T.Hiyama and H.Yamamoto,Tetrahedron Lett., 1978, 3051.
J.E.Boldwin,J.Chem.Soc.,Chem.Communs, 1976, 734.
T.Naya, M.Kotake,Tetrahedron Lett., 1968, 1645.
T.Imagawa, N.Murai, T.Akiyma, and M.Kawanisi,Tetrahedron Lett., 1979, 1691; C.R.Johnson, R.C.Elliot, and N.A.Meanwell,Ibid., 1982,23, 5005.
P. de Mayo,Mono- and Sesquiterpenoids. The Higher Terpenoids, Interscience Publishers, New York-London, 1959; W.F.Erman,Studies in Organic Chemistry, Ed. P.G.Gassman, Marcel Dekker, 1985,11A, 725.
A.J.Mancuso and D.Swern.Synthesis, 1981, 165.
A.M.Moiseenkov, V.A.Dragan, and V.V.Veselovsky.Izv. Akad.Nauk SSSR. Ser.Khim., 1989, 365 [Bull.Acad.Sci. USSR, Div.Chem.Sci., 1989,38, 314].
E.E. van Tamelen and T.J.Curphey,Tetrahedron Lett., 1962, 121.
K.Sato, O.Miyamoto, S.Inoue, and Y.Yamamoto,J.Chem. Soc., Chem.Communs., 1982, 153.
H.Schmidt,Chem.Ber., 1947,80, 528, 533.
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Deceased Nov., 1, 1992.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 113–117, January, 1993.
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Veselovsky, V.V., Moiseenkov, A.M. A short synthesis of some monoterpenoids from the adduct of myrcene with benzenesulfinyl chloride. Russ Chem Bull 42, 102–106 (1993). https://doi.org/10.1007/BF00699986
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DOI: https://doi.org/10.1007/BF00699986