Advertisement

Microwave-Assisted Natural Product Chemistry

  • Prasad Appukkuttan
  • Erik Van der EyckenEmail author
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 266)

Abstract

An overview of the application of microwave irradiation in natural product synthesis is presented, focusing on the developments in the last 5–10 years. This contribution covers the literature concerning the total synthesis of natural products and their analogues, the synthesis of alkaloids and the construction of building blocks of interest for natural product synthesis. As microwave irradiation appeared on the scene only recently, we are at an early stage of its application in natural product chemistry, even though some nice examples have been communicated recently. The application of dedicated microwave instruments as well as domestic microwave ovens is discussed, giving emphasis to the microwave-enhanced transformations.

Alkaloids Microwave irradiation Natural products Steroids Total synthesis 

Abbreviations

Boc

tert-butoxycarbonyl

CNS

central nervous system

m-CPBA

m-chloroperbenzoic acid

CTH

catalytic transfer hydrogenation

o-DCB

o-dichlorobenzene

DDQ

2,3-dichloro-5,6-dicyano-1,4-benzoquinone

DMF

N,N-dimethylformamide

DMSO

dimethyl sulfoxide

HIV

human immunodeficiency virus

IEDDA

inverse electron-demand Diels–Alder

PEA

phenethylamine

PMB

p-methoxybenzyl

PTSA

p-toluene sulfonic acid

RCAM

ring-closing alkyne metathesis

RCM

ring-closing metathesis

TBAF

N,N,N,N-tetrabutylammonium fluoride

TBDMS

tert-butyl dimethyl silyl

THF

tetrahydrofuran

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Ridley DD, Ritchie E, Taylor WC (1970) Aust J Chem 23:147 Google Scholar
  2. 2.
    Lytollis W, Scannell RT, An H, Murty VS, Reddy KS, Barr JR, Hecht SM (1995) J Am Chem Soc 117:12683 Google Scholar
  3. 3.
    Singh US, Scannell RT, An H, Carter BJ, Hecht SM (1995) J Am Chem Soc 117:12691 Google Scholar
  4. 4.
    Scannell RT, Barr JR, Murty VS, Reddy KS, Hecht SM (1988) J Am Chem Soc 110:3650 Google Scholar
  5. 5.
    Fürstner A (2002) Chem Eur J 8:1856 Google Scholar
  6. 6.
    Agrofoglio LA, Nolan SP (2005) Topics Curr Med Chem 5:1541 Google Scholar
  7. 7.
    Nicolaou KC, Bulger PG, Sarlah D (2005) Angew Chem Int Ed 44:4490 Google Scholar
  8. 8.
    Grubbs RH (2004) Tetrahedron 60:7117 Google Scholar
  9. 9.
    Schmidt B, Hermanns J (2004) Topics Organometallic Chem 13:223 Google Scholar
  10. 10.
    Deiters A, Martin SF (2004) Chem Rev 104:2199 and references cited therein Google Scholar
  11. 11.
    Mulzer J, Oehler E (2004) Topics Organometallic Chem 13:269 Google Scholar
  12. 12.
    Diver ST, Giessert AJ (2004) Chem Rev 104:1317 Google Scholar
  13. 13.
    Furstner A, Davies PW (2005) Chem Commun, p 2307 Google Scholar
  14. 14.
    Thiel OR (2004) In: Transition Metals for Organic Synthesis. 2nd Ed. Wiley-VCH, Weinheim 1:321 Google Scholar
  15. 15.
    Michell SS, Rhodes D, Bushman FD, Faulkner D (2000) Org Lett 2:1605 Google Scholar
  16. 16.
    Kiyota H, Dixon DJ, Luscombe CK, Hettstedt S, Ley SV (2002) Org Lett 4:3223 Google Scholar
  17. 17.
    Dixon DJ, Ley SV, Reynolds DJ (2002) Chem Eur J 8:1621 Google Scholar
  18. 18.
    Gonzalez N, Rodriguez J, Jiminez C (1999) J Org Chem 64:5705 Google Scholar
  19. 19.
    Kashiwada Y, Yamazaki K, Ikeshiro Y, Yamasishi T, Fujioka T, Mihashi K, Mizuki K, Cosentino LM, Fowke K, Morris-Natschke SL, Lee K-H (2001) Tetrahedron 57:1559 Google Scholar
  20. 20.
    Mamoru E, Hiroshi E (1982) Jpn Kokai Tokko Koho JP 82–28:080 Google Scholar
  21. 21.
    Kang Y, Mei Y, Du Y, Jin Z (2003) Org Lett 5:4481 Google Scholar
  22. 22.
    Saimoto H, Yoshida K, Murakami T, Morimoto M, Sashiwa H, Shigemasa Y (1996) J Org Chem 61:6768 Google Scholar
  23. 23.
    Narkhede DD, Iyer PR, Iyer CSR (1989) J Nat Prod 52:502 Google Scholar
  24. 24.
    Brink AJ, Rall GJH, Breytenbach JC (1977) Phytochemistry 16:273 Google Scholar
  25. 25.
    Subburaj K, Katoch R, Murugesh MG, Trivedi GK (1997) Tetrahedron 53:12621 Google Scholar
  26. 26.
    Volkmann RA, Andrews GC, Johnson WS (1975) J Am Chem Soc 97:4777 Google Scholar
  27. 27.
    Corey EJ, Ohno M, Mitra RB, Vatakencherry PA (1964) J Am Chem Soc 86:478 Google Scholar
  28. 28.
    Lei B, Fallis AG (1993) J Org Chem 58:2186 Google Scholar
  29. 29.
    Abegaz BM (2002) Phytochem Rev 1:299 Google Scholar
  30. 30.
    Aguilar R, Benavides A, Tamariz J (2004) Synthetic Commun 34:2719 Google Scholar
  31. 31.
    Kad GL, Singh V, Khurana A, Singh J (1998) J Nat Prod 61:297 Google Scholar
  32. 32.
    Grainger RS, Patel A (2003) Chem Commun, p 1072 Google Scholar
  33. 33.
    Lewis FD, Reddy GD, Bassani DM (1993) J Am Chem Soc 115:6468 Google Scholar
  34. 34.
    Lewis FD, Reddy GD, Bassani DM, Schneider S, Gahr M (1994) J Am Chem Soc 116:597 Google Scholar
  35. 35.
    Subbaraju GV, Manhas MS, Bose AK (1991) Tetrahedron Lett 32:4871 Google Scholar
  36. 36.
    Ezaki M, Iwami M, Yamashita M, Hashimoto S, Komori T, Umehara K, Mine Y, Kohsaka M, Aoiki H, Imanaka H (1985) J Antibiot 38:1453 Google Scholar
  37. 37.
    Uchida I, Shigematsu N, Ezaki M, Hashimoto M, Hatsuo A, Hiroshi I (1985) J Antibiot 38:1462 Google Scholar
  38. 38.
    Uchida I, Ezaki M, Shigematsu N, Hashimoto M (1985) J Org Chem 50:1341 Google Scholar
  39. 39.
    Chang CC, Morton GO, James JC, Siegel MM, Kuck NA, Testa RT, Borders DB (1991) J Antibiot 44:674 Google Scholar
  40. 40.
    Lépine R, Zhu J (2005) Org Lett 7:2981 Google Scholar
  41. 41.
    Kappe CO (2004) Angew Chem Int Ed 43:6250 Google Scholar
  42. 42.
    Kappe CO (2002) Curr Opin Chem Biol 6:314 Google Scholar
  43. 43.
    Kappe CO, Dallinger D (2006) Drug Discov 5:51 Google Scholar
  44. 44.
    Ersmark K, Larhed M, Wannberg J (2004) Curr Opin Drug Discov Dev 7:417 Google Scholar
  45. 45.
    Mavandadi F, Lidstroem P (2004) Curr Top Med Chem 4:773 Google Scholar
  46. 46.
    Alexandre F-R, Domon L, Frere S, Testard A, Thiery V, Besson T (2003) Mol Diver 7:273 Google Scholar
  47. 47.
    Somei M, Yamada F (2005) Nat Prod Rep 22:73 Google Scholar
  48. 48.
    Somei M, Yamada F (2004) Nat Prod Rep 21:278 Google Scholar
  49. 49.
    Toyota M, Ihara M (1998) Nat Prod Rep 15:327, and references cited therein Google Scholar
  50. 50.
    Franco LH, Palermo JA (2003) Chem Pharm Bull 51:975 Google Scholar
  51. 51.
    Hernández FL, Bal de Kier JE, Puricelli L, Tatian M, Seldes AM, Palermo JA (1998) J Nat Prod 61:1130 Google Scholar
  52. 52.
    Butler MS, Capon RJ, Lu CC (1992) Aust J Chem 45:1871 Google Scholar
  53. 53.
    Perry NB, Ettouati L, Litaudon M, Blunt JW, Munro MHG, Parkin S, Hope H (1994) Tetrahedron 50:3987 Google Scholar
  54. 54.
    Rauwald HW, Kobar M, Mutschler E, Lambrecht G (1992) Planta Med 58:486 Google Scholar
  55. 55.
    Sharaf MH M, Schiff PL Jr, Tackie AN, Phoebe CH Jr, Martin GE (1996) J Heterocycl Chem 33:239 Google Scholar
  56. 56.
    Cimanga K, De Bruyne T, Pieters L, Claeys M, Vlietinck A (1996) Tetrahedron Lett 37:1703 Google Scholar
  57. 57.
    Cimanga K, De Bruyne T, Pieters L, Claeys M, Vlietinck A (1997) J Nat Prod 60:688 Google Scholar
  58. 58.
    Fresneda PM, Molina P, Delgado S (2001) Tetrahedron 51:6197 Google Scholar
  59. 59.
    Kumemura T, Choshi T, Hirata A, Sera M, Takahashi Y, Nobuhiro J, Hibino S (2005) Chem Pharm Bull 53:393 Google Scholar
  60. 60.
    Kohno J, Hiramatsu H, Nishio M, Sakurai M, Okuda T, Komatsubara S (1999) Tetrahedron 55:11247 Google Scholar
  61. 61.
    Kohno J, Sakurai M, Kameda N, Nishio M, Kawano K, Kishi N, Okuda T, Komatsubara S (1999) J Antibiot 52:913 Google Scholar
  62. 62.
    Kumemura T, Choshi T, Hirata A, Sera M, Takahashi Y, Nobuhiro J, Hibino S (2003) Heterocycles 61:13 Google Scholar
  63. 63.
    Pouìlhes A, Langlois Y, Chiaroni A (2003) Synlett, p 1488 Google Scholar
  64. 64.
    Cox ED, Cook JM (1995) Chem Rev 95:1797 Google Scholar
  65. 65.
    Foderato TA, Barrows LR, Lassota P, Ireland CM (1997) J Org Chem 62:6064 Google Scholar
  66. 66.
    Ma ZZ, Hano Y, Nomura T, Chen JJ (1997) Heterocycles 46:541 Google Scholar
  67. 67.
    Slichenmyer WJ, Rowinsky EK, Donehower RC, Kaufmann SH (1993) J Nat Cancer Inst 85:271 Google Scholar
  68. 68.
    Yadav JS, Reddy BVS (2002) Tetrahedron Lett 43:1905 Google Scholar
  69. 69.
    Lipińska T (2002) Tetrahedron Lett 43:9565 Google Scholar
  70. 70.
    Costa-Campos L, Lara DR, Nunes DS, Elisabetsky E (1998) Pharmacol Biochem Behav 60:133 Google Scholar
  71. 71.
    Lipińska T, Guibe-Jampel E, Petit A, Loupy A (1999) Synth Commun 29:1349 Google Scholar
  72. 72.
    Beljanski M, Crochet S (1996) Int J Oncol 8:1143 and references cited therein Google Scholar
  73. 73.
    Rykowski A, Lipińska T (1997) Pol J Chem 71:83 Google Scholar
  74. 74.
    Lipińska T (2004) Tetrahedron Lett 45:8831 Google Scholar
  75. 75.
    Lipińska T (2005) Tetrahedron 61:8148 Google Scholar
  76. 76.
    Wolkenberg SE, Wisnoski DD, Leister WH, Wang Y, Zhao ZJ, Lindsley CW (2004) Org Lett 6:1453 Google Scholar
  77. 77.
    Cui B, Zheng BL, He K, Zheng QY J (2003) Nat Prod 66:1101 Google Scholar
  78. 78.
    Liu J-F, Lee J, Dalton AM, Bi G, Yu L, Baldino CM, McElory E, Brown M (2005) Tetrahedron Lett 46:1241 Google Scholar
  79. 79.
    Wolfe JF, Rathman TL, Sleevi MC, Campbell JA, Greenwood TD (1990) J Med Chem 33:161 Google Scholar
  80. 80.
    Buzas A, Hoffmann C (1959) Bull Soc Chim Fr, p 1889 Google Scholar
  81. 81.
    Welch WM, Ewing FE, Huang J, Menniti FS, Pagnozzi MJ, Kelly K, Seymour PA, Guanowsky V, Guhan S, Guinn MR, Critchett D, Lazzaro J, Ganong AH, DeVries KM, Staigers TL, Chenard BL (2001) Bioorg Med Chem Lett, p 177 Google Scholar
  82. 82.
    Liu J-F, Kaselj M, Isome Y, Ye P, Sargent K, Sprague K, Cherrak D, Wilson CJ, Si Y, Yohannes D, Ng S-C (2006) J Comb Chem 8:7 Google Scholar
  83. 83.
    Penn J, Mantle PG, Bilton JN, Sheppard RN (1992) J Chem Soc, Perkin Trans 1, p 1495 Google Scholar
  84. 84.
    Numata A, Takahashi C, Matsushita T, Miyamoto T, Kawai K, Usami Y, Matsumura E, Inoue M, Ohishi H, Shingu T (1992) Tetrahedron Lett 33:1621 Google Scholar
  85. 85.
    Takahashi C, Matsushita T, Doi M, Minoura K, Shingu T, Kumeda Y, Numata A (1995) J Chem Soc, Perkin Trans 1, p 2345 Google Scholar
  86. 86.
    Liu J-F, Ye P, Zhang B, Bi G, Sargent K, Yu L, Yohannes D, Baldino CM (2005) J Org Chem 70:6339 Google Scholar
  87. 87.
    Tietze LF (1996) Chem Rev 96:115 Google Scholar
  88. 88.
    Tietze LF, Haunert F (2000) In: Shibasaki M, Stoddart JF, Vögtle F (eds) Stimulating Concepts in Chemistry. Wiley, Weinheim, p 39 Google Scholar
  89. 89.
    Liu J-F, Ye P, Sprague K, Sargent K, Yohannes D, Baldino CM, Wilson CJ, Ng S-C (2005) Org Lett 7:3363 Google Scholar
  90. 90.
    Liu J-F, Kaselj M, Isome Y, Chapnick J, Zhang B, Bi G, Yohannes D, Yu L, Baldino CM (2005) J Org Chem 70:10488 Google Scholar
  91. 91.
    Goetz MA, Monaghan RL, Chang RSL, Ondeyka J, Chen TB, Lotti VJ (1988) J Antibiot 41:875 Google Scholar
  92. 92.
    Sun HH, Barrow CJ, Sedlock DM, Gillum AM, Cooper R (1994) J Antibiot 47:515 Google Scholar
  93. 93.
    Pla D, Marchal A, Olsen CA, Albericio F, Alvarez M (2005) J Org Chem 70:8231 Google Scholar
  94. 94.
    Cironi P, Albericio F, Alvarez M (2004) In: Gribble GW, Joule JA (eds) Progress in Heterocyclic Chemistry. Pergamon, Oxford, UK, vol 16, p 1 Google Scholar
  95. 95.
    Facompré M, Tardy C, Bal-Mahieu C, Colson P, Pérez C, Manzanares I, Cuevas C, Bailly C (2003) Cancer Res 63:7392 Google Scholar
  96. 96.
    Sharma U, Bora U, Boruah RC, Sandhu JS (2002) Tetrahedron Lett 43:143 Google Scholar
  97. 97.
    Longchar M, Bora U, Boruah RC, Sandhu JS (2002) Synthetic Commun 32:3611 Google Scholar
  98. 98.
    Skoda-Földes R, Pfeiffer P, Horváth J, Tuba Z, Kollár L (2002) Steroids 67:709 Google Scholar
  99. 99.
    Skoda-Földes R, Kollár L, Heil B, Gálik G, Tuba Z, Arcadi A (1991) Tetrahedron Asymm 2:633 Google Scholar
  100. 100.
    Skoda-Földes R, Csákai Z, Kollár L, Horváth J, Tuba Z (1995) Steroids 60:812 Google Scholar
  101. 101.
    Das B, Venkataiah B, Kashinatham A (1999) Tetrahedron 55:6585 Google Scholar
  102. 102.
    Kupchan SM, Eakin MA, Thomas AM (1971) J Med Chem 14:1147 Google Scholar
  103. 103.
    Mew D, Baiza F, Towers GHN, Levy JG (1982) Planta Med 45:23 Google Scholar
  104. 104.
    Picman AK, Towers GHN (1983) Biochem Syst Ecol 11:321 Google Scholar
  105. 105.
    Sharma GL, Bhutani KK (1988) Planta Med 54:120 Google Scholar
  106. 106.
    Hopper M, Kirby GC, Kulkarni MM, Kulkarni SN, Nagasampagi BA, O'Neill MJ, Philipson JD, Rojatkar SR, Warhurs DC (1990) Eur J Med Chem 25:717 Google Scholar
  107. 107.
    Gallo ILC, Whang-peng J, Adamson ILK (1971) J Nat Cancer Inst 46:789 Google Scholar
  108. 108.
    Wall ME, Wani MC (1977) Ann Rev Pharmacol Toxicol 17:117 Google Scholar
  109. 109.
    Pendrak I, Wittrock R, Kingsbury WD (1995) J Org Chem 60:2912 Google Scholar
  110. 110.
    Pendrark I, Berney S, Wittrock R, Lambert DM, Kingsbury WD (1994) J Org Chem 59:2623 Google Scholar
  111. 111.
    Das B, Madhusudhan P, Kashinatham A (1998) Tetrahedron Lett 39:431 Google Scholar
  112. 112.
    Das B, Srinivas KVNS (2002) Synth Commun 32:3027 Google Scholar
  113. 113.
    Buckingham J (ed) (1994) Dictionary of Natural Products. 1st Ed. Chapman and Hall, London, vol 1, p 640 Google Scholar
  114. 114.
    Gharbi SA, Beal JL, Doskotch RW, Mitscher LA (1973) Lloydia 36:349 Google Scholar
  115. 115.
    Das B, Srinivas KVNS (2004) Synth Commun 34:199 Google Scholar
  116. 116.
    Baran PS, O'Malley DP, Zografos AL (2004) Angew Chem Int Ed 43:2674 Google Scholar
  117. 117.
    Borrelli F, Campagnuolo C, Capasso R, Fattorusso E, Taglialatela-Scafati O (2004) Eur J Org Chem 15:3227 Google Scholar
  118. 118.
    Campagnuolo C, Fattorusso E, Taglialatela-Scafati O (2003) Eur J Org Chem 2:284 Google Scholar
  119. 119.
    Lindsley CW, Wisnoski DD, Wang Y, Leister WH, Zhao Z (2003) Tetrahedron Lett 44:4495 Google Scholar
  120. 120.
    Ohmoto T, Koike K (1989) In: Brossi A (ed) The Alkaloids. Academic Press, New York, vol 36, p 135 Google Scholar
  121. 121.
    Haynes HF, Nelson ER, Price JR (1952) Aust J Sci Res Ser A 5:387 Google Scholar
  122. 122.
    Nelson ER, Price JR (1952) Aust J Sci Res Ser A 5:563 Google Scholar
  123. 123.
    Nelson ER, Price JR (1952) Aust J Sci Res Ser A 5:68 Google Scholar
  124. 124.
    Anderson LA, Harris A, Phillipson JD (1983) J Nat Prod 46:374 Google Scholar
  125. 125.
    Arisawa M, Kinghorn AD, Cordell GA, Farnsworth NR (1983) J Nat Prod 46:222 Google Scholar
  126. 126.
    Ohmoto T, Nikaido T, Koide K, Kohda K, Sankawa U(1988) Chem Pharm Bull 36:4588 Google Scholar
  127. 127.
    Ouyang Y, Koide K, Ohmoto T (1994) Phytochemistry 36:1543 Google Scholar
  128. 128.
    Benson SC, Li J-H, Snyder JK (1992) J Org Chem 57:5285 Google Scholar
  129. 129.
    Lindsley CW, Bogusky MJ, Leister WH, McClain RT, Robinson RG, Barnett SF, Defeo-Jones D, Ross CW, Hartman GD (2005) Tetrahedron Lett 46:2779 Google Scholar
  130. 130.
    Chérouvrier J-R, Carreaux F, Bazureau JP (2002) Tetrahedron Lett 43:3581 Google Scholar
  131. 131.
    Cafieri F, Fattorusso E, Mangani A, Tagliakatela-Scafati O (1996) Tetrahedron Lett 37:3587 Google Scholar
  132. 132.
    Boehm JC, Gleason JG, Pendrak I, Sarau HM, Schmidt B, Foley JJ, Kingsbury WD (1993) J Med Chem 36:3333 Google Scholar
  133. 133.
    Kuo F-M, Tseng M-C, Yen Y-H, Chu Y-H (2004) Tetrahedron 60:12075 Google Scholar
  134. 134.
    Horiguchi Y, Nakamura M, Saitoh T, Sano T (2003) Chem Pharm Bull 51:1368 Google Scholar
  135. 135.
    Horiguchi Y, Nakamura M, Kida A, Kodama H, Saitoh T, Sano T (2003) Heterocycles 59:691 Google Scholar
  136. 136.
    Cheng CC, Chu Y-H (1999) J Comb Chem 1:461 Google Scholar
  137. 137.
    Papadopoulou D, Spyros IP, Varvoglis A (1998) Tetrahedron Lett 39:2865 Google Scholar
  138. 138.
    Mayer JP, Bankaitis-Davis D, Zhang J, Beaton G, Bjergarde K, Anderson CM, Goodman BA, Herrera CJ (1996) Tetrahedron Lett 37:5633 Google Scholar
  139. 139.
    Horiguchi Y, Kodama H, Nakamura M, Yoshimura T, Hanezi K, Hamada H, Saitoh T, Sano T (2002) Chem Pharm Bull 50:253 Google Scholar
  140. 140.
    Tseng M-C, Liang Y-M, Chu Y-H (2005) Tetrahedron Lett 46:6131 Google Scholar
  141. 141.
    Tietze LF, Wiegand JM, Vock CA (2004) Eur J Org Chem, p 4107 Google Scholar
  142. 142.
    Micheli RA, Hajos ZG, Cohen N, Parrish DR, Portland LA, Sciamanna W, Scott MA, Wehrli PA (1975) J Org Chem 40:675 Google Scholar
  143. 143.
    Eder U, Sauer G, Wiechert R (1971) Angew Chem 83:492 Google Scholar
  144. 144.
    Eder U, Sauer G, Wiechert R (1971) Angew Chem Int Ed Engl 10:496 Google Scholar
  145. 145.
    Kupchan SM, Britton RW, Ziegler MF, Gilmore CJ, Restivo RJ, Bryan RF (1973) J Am Chem Soc 95:1335 Google Scholar
  146. 146.
    Wang RW, Rebhum LI, Kupchan SM (1977) Cancer Res 37:3071 Google Scholar
  147. 147.
    Sackett DL (1993) Pharmacol Ther 59:163 Google Scholar
  148. 148.
    Zavala F, Guenard D, Robin J-P, Brown E (1980) J Med Chem 23:546 Google Scholar
  149. 149.
    Tomioka K, Kubota Y, Kawasaki H, Koga K (1989) Tetrahedron Lett 30:2949 Google Scholar
  150. 150.
    Kubota Y, Kawasaki H, Tomioka K, Koga K (1993) Tetrahedron 49:3081 Google Scholar
  151. 151.
    Beryozkina T, Appukkuttan P, Mont N, Van der Eycken E (2006) Org Lett 8:487 Google Scholar
  152. 152.
    Miyaura N, Suzuki A (1995) Chem Rev 95:2457 Google Scholar
  153. 153.
    Diederich F, Stang PJ (eds) (1998) Metal-Catalyzed Cross-coupling Reactions. Wiley, Weinheim, p 517 Google Scholar
  154. 154.
    Suzuki A (1999) J Organometallic Chem 576:147 Google Scholar
  155. 155.
    Kotha S, Lahiri K, Kashinath D (2002) Tetrahedron 58:9633 Google Scholar
  156. 156.
    Leadbeater NE (2005) Chem Commun 23:2881 Google Scholar
  157. 157.
    Apukkuttan P, Van der Eycken E, Dehaen W (2005) Synlett, p 127 Google Scholar
  158. 158.
    Appukkuttan P, Orts AB, Chandran RP, Goeman JL, Van der Eycken J, Dehaen W, Van der Eycken E (2004) Eur J Org Chem, p 3277 Google Scholar
  159. 159.
    Ishida Y, Sasaki Y, Kimura Y, Watanabe K (1985) J Pharmacobiodyn 8:917 Google Scholar
  160. 160.
    Ishida Y, Sadamune K, Kobayashi S, Kihara M (1983) J Pharmacobiodyn 6:391 Google Scholar
  161. 161.
    Viladomat F, Bastida J, Codina C, Campbell WE, Mathee S (1995) Phytochemistry 40:307 Google Scholar
  162. 162.
    Hoarau C, Couture A, Deniau E, Grandclaudon P (2002) J Org Chem 67:5846 Google Scholar
  163. 163.
    Patil PA, Snieckus V (1998) Tetrahedron Lett 39:1325 Google Scholar
  164. 164.
    Sahakitpichan P, Ruchiravat S (2003) Tetrahedron Lett 44:5239 Google Scholar
  165. 165.
    Lidström P, Tierney J, Wathey B, Westman J (2001) Tetrahedron 57:9225 Google Scholar
  166. 166.
    Lidström P, Westman J, Lewis A (2002) Comb Chem High Throughput Screening 6:441 Google Scholar
  167. 167.
    Larhed M, Moberg C, Hallberg A (2002) Acc Chem Res 35:717 Google Scholar
  168. 168.
    Loupy A (2002) Microwaves in Organic Synthesis. Wiley, Weinheim, Germany, and references therein Google Scholar
  169. 169.
    Kappe CO (2004) Angew Chem Int Ed 43:6250 Google Scholar
  170. 170.
    Hayes BL (2004) Aldrichim Acta 37:66 Google Scholar
  171. 171.
    Appukkuttan P, Dehaen W, Van der Eycken E (2005) Org Lett 7:2723 Google Scholar
  172. 172.
    Cledera P, Sánchez JD, Caballero E, Avendaño C, Ramos MT, Menéndez JC (2004) Synlett, p 803 Google Scholar
  173. 173.
    Hochlowski JE, Mullally MM, Spanton SG, Whittern DN, Hill P, McAlpine JB (1993) J Antibiotics 46:380 Google Scholar
  174. 174.
    Barrow CJ, Sun HH (1994) J Nat Prod 57:471 Google Scholar
  175. 175.
    Lu Y-F, Fallis AG (1993) Tetrahedron Lett 34:3367 Google Scholar
  176. 176.
    Wani MC, Taylor HL, Wall ME, Coggan P, McPhail AT (1971) J Am Chem Soc 93:2325 Google Scholar
  177. 177.
    Pamess J, Horwitz SB (1981) J Cell Biol 91:479 Google Scholar
  178. 178.
    Chapin SJ, Bulinski JC, Gundersen GG (1991) Nature 349:24 Google Scholar
  179. 179.
    Torres G, Torres W, Prieto JA (2004) Tetrahedron 60:10245 Google Scholar
  180. 180.
    Corey EJ, Hase T (1979) Tetrahedron Lett 20:335 Google Scholar
  181. 181.
    Lipshutz BH, Kozlowski J (1984) J Org Chem 49:1147 Google Scholar
  182. 182.
    Lipshutz BH, Barton JC (1988) J Org Chem 53:4495 Google Scholar
  183. 183.
    Mohr P (1992) Tetrahedron Lett 33:2455 Google Scholar
  184. 184.
    Burova SA, McDonald FE (2002) J Am Chem Soc 124:8188 Google Scholar
  185. 185.
    Martin HJ, Drescher M, Mulzer J (2000) Angew Chem Int Ed 39:581 Google Scholar
  186. 186.
    Wang Z, Schreiber SL (1990) Tetrahedron Lett 31:312 Google Scholar
  187. 187.
    Rinehart K, Maheshwari ML, Antosz FJ, Mathur HH, Sasaki K, Schacht RJ (1971) J Am Chem Soc 93:6273 Google Scholar
  188. 188.
    Rinehart KL, Antosz FJ, Sasaki K, Martin PK, Maheshwari ML, Reussre F, Li HL, Moran D, Wiley PF (1974) Biochemistry 13:861 Google Scholar
  189. 189.
    Miyashita M, Shiratani T, Kawamine K, Hatakeyama S, Miyazawa M, Irie H (1996) Chem Commun, p 1027 Google Scholar
  190. 190.
    Banik BK, Barakat KJ, Wagle DR, Manhas MS, Bose AK (1999) J Org Chem 64:5746 Google Scholar
  191. 191.
    Sharma A, Kumar V, Sinha AK (2006) Adv Synth Catal 348:354 Google Scholar
  192. 192.
    Arefalk A, Larhed M, Hallberg A (2005) J Org Chem 70:938 Google Scholar
  193. 193.
    Berthold H, Schotten T, Honig H (2002) Synthesis 11:1607 Google Scholar
  194. 194.
    Daga MC, Taddei M, Varchi G (2001) Tetrahedron Lett 42:5191 Google Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2006

Authors and Affiliations

  1. 1.Department of Medicinal ChemistryOrganic Pharmaceutical Chemistry, BMC, Uppsala UniversityUppsalaSweden
  2. 2.Department of ChemistryUniversity of LeuvenLeuvenBelgium

Personalised recommendations