A synthetic approach to terpendoles: Decahydrobenzo[f]chromenes by an intermolecular Diels-Alder route

Arkivoc

Volumn 2011, Issue 2, 2011, Pages 355-362

  Basu, Debjit ^a   Chandrasekharam, Malapaka ^a   Mainkar, Prathama S ^a   Chandrasekhar, Srivari ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Decahydro 1h benzo f chromene system; Indole diterpenoid; Intermolecular diels alder reaction; Pyran ring

Indexed keywords

EID: 79953211591     PISSN: 1551-7012     EISSN: 15517004     Source Type: Journal    
DOI: 10.3998/ark.5550190.0012.229     Document Type: Article

References (33)

1. (a) Betina, V. Mycotoxins: Chemical, Biological, and Environmental Aspects; Elsevier: New York, 1989: Vol. 9.
2. (b) Turner, W. B.; Aldridge, D. C. Fungal Metabolites II: Academic Press: London, 1983.
3. Li, C.; Gloer, J. B.; Wicklow, D. T.; Dowd, P. F. Org. Lett. 2002, 4, 3095 and references cited there in.
4. Kimura, Y.; Nishibe, M.; Nakajima, H.; Hamasaki, T.; Shigemitsu, N.; Sugawara, F.; Stout, T. J.; Clardy, J. Tetrahedron Lett. 1992, 33, 6987.
5. Acklin, W.; Weibel, F.; Arigoni, D. Chimia 1977, 31, 63.
6. De Jesus, E.; Gorst-Allman, P.; Steyn, S.; Van Heerden, R.; Vleggaar, R.; Wessels, L.; Hull, W. E. J. Chem.. Soc., Perkin Trans. 1 1983, 1863.
7. Laws, I.; Mantle, G. J. Gen. Microbiol. 1989, 135, 2679.
8. Byrne, M.; Smith, K.; Ondeyka, G. J. Am. Chem. Soc, 2002, 124, 7055.
9. Munday-Finch, C.; Wilkins, L.; Miles, O. Phytochemistry 1996, 41, 327.
10. (a) Springer J. P.; Clardy J. Tetrahedron Lett. 1980, 21, 231.
11. (b) Cole R. J.; Kirksey J. W.; Wells J. M. Can. J. Microbiol. 1974, 8, 1159.
12. (c) Nozawa K.; Nakajima S.; Kawai K. J. Chem. Soc., Perkin Trans 1 1988, 2607.
13. (d) Gallagher R. T.; Finer J.; Clardy J.; Leutweiler A.; Weibel F.; Acklin W.; Arogoni D. Tetrahedron Lett. 1980, 21, 235.
14. (e) Gallagher R. T.; Clardy J.; Wilson B. J. Tetrahedron Lett. 1980, 21, 239.
15. (f) Cole R. J.; Dorner J. W.; Lamsden J. A.; Cox R. H.; Pape C.; Cunfer B.; Nicolson S. S.; Bedell D. M. J. Agric. Food Chem. 1977, 25, 1197.
16. (g) De Jesus A. E.; Gorstallman C. P.; Steyn P. S.; Vanheerden F. R.; Vleggaa R.; Wessels P. L.; Hull W. E. J. Chem. Soc., Perkin Trans. 1 1983, 1847.
17. (h) Penn J.; Swift R.; Wigley L. J.; Mantlep P. G.; Bilton J. N.; Sheppard R. N. Phytochemistry 1993, 32, 1431.
18. (i) Munday-Finch S. C.; Wilkins A. L.; Miles C. O. J. Agric. Food Chem. 1998, 46, 590.
19. (j) Penn J.; Biddle J. R.; Mantle P. G.; Bilton J. N.; Sheppard R. N. J. Chem. Soc., Perkin Trans. 1 1992, 23.
20. (k) Laakso J. A.; Gloer J. B.; Wicklow D. T.; Dowd P. F. J. Org. Chem. 1992, 57, 2066.
21. (l) Belofsky G. N.; Gloer J. B.; Wicklow D. T.; Dowd P. F. Tetrahedron 1995, 51, 3959.
22. (m) Nakazawa J.; Yajima J.; Usul T.; Ueki M.; Takasuki A.; Imoto M.; Toyoshima Y. Y.; Osada H. Chemistry & Biology 2003, 10, 131.
23. (n) Miles C. O.; Wilkins A. L.; Garthwaute I.; Ede R. M.; Munday-Finch S. C. J. Org. Chem. 1995, 60, 6067.
24. (o) Ondeyka J. G.; Helms G. L.; Hensens O. D.; Goetz M. A.; Zink D. L.; Tsipouras A. ; Shoop W. L.; Slayton L.; Dombrowski A. W.; Polishook J. D.; Ostlind D. A.; Tsou N. N.; Ball R. G.; Singh S. B. J. Am. Chem. Soc. 1997, 119, 8809.
25. (p) Nail J. T.; Mantle P. G.; Sheppard R. N.; Weight E. S. J. Chem. Soc., Perkin Trans. 1 1995, 1121.
26. (q) Li. C.; Gloer J. B. ; Wicklow D. T.; Dowd P. F. Org. Lett. 2002, 4, 3095.
27. Huang, X-H.; Tomoda, H.; Nishida, H.; Masuma, R.; Omura, S. J. Antibiot. 1995, 48, 1.
28. Nakazawa, J.; Yajima, J.; Usul, T.; Ueki, M.; Takatsuki, A.; Imoto, M.; Toyoshima, Y. Y.; Osada, H. Chemistry Biology 2003, 10, 131.
29. Ogata, M.; Ueda, J-Y.; Hoshi, M.; Hashimoto, J.; Nakashima, T.; Anzai, K.; Takagi, M.; Kazuo S-Y. J. Antibiot. 2007, 60, 645.
30. (a) Smith, A. B. III, Toshiaki, S., Tamara, L. L., Jill, K.-W.; J. Am. Chem. Soc. 1990, 112, 8197.
31. (b) Smith A. B. III; Haifeng, C., Helv. Chim. Acta 2003, 86, 3908.
32. (c) Smith, A. B. III, Akin H. D., László, K., Org. Lett. 2006, 8, 1665.
33. Chemical equation presented.