Drimane homochiral semisynthesis: Pereniporin A, 9-epi-warburganal and c-9 nitrogenated drimanes

Natural Product Letters

Volumn 11, Issue 2, 1998, Pages 145-152

  Urones, J G ^a   Diez D ^a   Gomez P M ^a   Marcos, I S ^a   Basabe, P ^a   Moro, R F ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

Author keywords

9 epi warburganal; C 9 nitrogenated drimanes; Drimane; Halimium viscosum; Labdane; Pereniporin A; Zamoranic acid

Indexed keywords

ALKADIENE; DRIMANE; NATURAL PRODUCT; NITROGEN DERIVATIVE; UNCLASSIFIED DRUG; WARBURGANAL;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL STRUCTURE; PRECURSOR; SYNTHESIS;

EID: 0345020393     PISSN: 10575634     EISSN: None     Source Type: Journal    
DOI: 10.1080/10575639808041211     Document Type: Article

References (31)

1. J. G. Urones, I. S. Marcos, B. G. Pérez, A. M. Ligthow, David Díez, P. M. Gómez, P. Basabe and N. M. Garrido, Tetrahedron, 1995, 51, 1845-1860 and references cited therein.
2. a) J. G. Urones, I. S. Marcos, B. G. Pérez, D. Díez, A. M. Ligthow, P. M. Gómez, P. Basabe and N. M. Garrido, Tetrahedron, 1994, 50, 10995-11012.
3. b) J. G. Urones, I. S. Marcos, B. G. Pérez, A. M. Ligthow, David Díez, P. Basabe and P. M. Gómez, Tetrahedron Lett., 1994, 35, 3781-3784.
4. c) T. Nakano and M. A. Maillo, Synth. Commun., 1981, 11, 463-473.
5. a) B. J. M. Jansen and A. de Groot, Nat. Prod. Rep., 1991, 309-318.
6. b) T. Kida, H. Shibai and H. Seto, J. Antibiot., 1986, 39, 613-15.
7. c) H. Morioka, M. Ishihara, M. Takezawa, K. Hirayama, E. Suzuki, Y. Komoda and H. Shibai, Agric. Biol. Chem., 1985, 49, 1365-70.
8. A. S. Kende and T. J. Blacklock, Tetrahedron Lett., 1980, 21, 3119-3122.
9. a) K. Mon and H. Takaishi, Liebigs Ann. Chem., 1989, 939-943.
10. b) L. F. Fieser, J. Am. Chem. Soc., 1948, 70, 3237-3244.
11. c) K. Nakanishi and L. F. Fieser, J. Am. Chem. Soc., 1952, 74, 1952.
12. d) M. Cortés, J. López and E. Díaz, Nat. Prod. Lett., 1993, 21, 37.
13. A. L. Gemal and J. L. Luche, Tetrahedron Lett., 1981, 22, 4077-4080.
14. a) D. Askin, D. Angst and S. Danishefsky, J. Org. Chem., 1987, 52, 622-635.
15. b) R. E. Ireland, D. W. Norbeck, G. S. Mandel and N. S. Mandel, J. Am. Chem. Soc., 1985, 107, 32853294.
16. c) S. Hanessian, P. J. Roy, M. Petrini, P. J. Hudges, R. Di Fabio and G. Carganico, J. Org. Chem., 1990, 55, 5766-5777.
17. d) Y. Nishikimi, T. Iimori, M. Sodeoka and M. Shibasaki, J. Org. Chem., 1989, 54, 3354-3359.
18. e) H. Emde, D. Domsch, H. Feger and U. Frick, Synthesis, 1982, 1.
19. f) E. J. Corey, H. Cho, C. Rücker and D. H. Hua, Tetrahedron Lett., 1981, 22, 3455.
20. g) E. J. Corey and N. M. Mehrota, J. Am. Chem. Soc., 1984, 106, 3384-3384.
21. a) K. Omura and D. Swern, Tetrahedron, 1978, 34, 1651-1660.
22. b) A. J. Mancuso and D. Swern, Synthesis, 1981, 165-185.
23. E. J. Corey and B. B. Snider, J. Am. Chem. Soc., 1972, 94, 2549-2550.
24. K. S. Keshava Murthy and D. N. Dhar, Synth. Commun., 1984, 14, 687-695.
25. a) E. Wenkert, T. Hudlicky and H. D. H. Showalter, J. Am. Chem. Soc., 1978, 100, 4893-4894.
26. b) T. Hayashi, A. Yamamoto and Y. Ito, Tetrahedron Lett., 1988, 29, 99-102.
27. N. Ardabilchi, A. O. Fitton, J. R. Frost, F. K. Oppong-Boachie, A. H. b. A. Hadi and A. b. M. Sharif, J. Chem. Soc., Perkin Trans. 1, 1979, 539-543.
28. a) T. Kunieda, T. Ishizuka, T. Higuchi and M. Hirobe, J. Org. Chem., 1988, 53, 3381-3383.
29. nd edition, Ed. John Wiley & Sons, New York, 1991.
30. c) T. Ishizuka and T. Kunieda, Tetrahedron Lett., 1987, 28, 4185-4188.
31. d) D. A. Evans and A. E. Weber, J. Am. Chem. Soc., 1987, 109, 7151-7157.