Total syntheses of (-)-papuamine and (-)-haliclonadiamine

Journal of Organic Chemistry

Volumn 61, Issue 2, 1996, Pages 700-709

  McDermott, Todd S ^a   Mortlock, Andrew A ^a   Heathcock, Clayon H ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ANTIFUNGAL AGENT; HALICLONADIAMINE; PAPUAMINE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030043643     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951647i     Document Type: Article

References (25)

1. Scheuer, P. J.; Baker, B. J.; Shoolery, J. N. J. Am. Chem. Soc. 1988, 110, 965.
2. Faulkner, D. J.; Fahy, E.; Molinski, T. F.; Harper, M. K.; Sullivan, B. W Tetrahedron Lett. 1988, 29, 3427.
3. Barrett, A. G. M.; Boys, M. L.; Boehm, T. L. J. Chem. Soc., Chem. Commun. 1994, 1881-1882.
4. Weinreb, S. M.; Borzilleri, R. M.; Parvez, M. J. Am. Chem. Soc. 1994, 116, 9789-9790.
5. Cram, D. J.; Elhafez, F. A. A. J. Am. Chem. Soc. 1952, 74, 5828-5835
6. Felkin, H.; Cherest, M.; Prudent, N. Tetrahedron Lett. 1968, 2199-2204.
7. Heathcock, C. H.; Davis, B. R.; Hadley, C. R. J. Med. Chem. 1989, 32, 197-202.
8. Seyferth, D.; Marmor, R. S.; Hubert, P. J. Org. Chem. 1971, 36, 1379.
9. Colvin, E. W.; Hamill, B. J. J. Chem. Soc., Perkin Trans. I 1977, 869.
10. Gilbert, J. C.; Weerasooriya, U. J. Org. Chem. 1979, 44, 4997.
11. Schwartz, J.; Hart, D. W. J. Am. Chem. Soc. 1974, 96, 8115.
12. Buchwald, S. J.; LaMaire, S. J.; Neilsen, R. B.; Watson, B. T.; King, S. M. Org. Synth. 1992, 71, 77.
13. Negishi, E.; Takahashi, T. Aldrichimica Acta 1985, 18, 31.
14. Borch, R. F.; Bernstein, M. D.; Durst, H. D. J. Am. Chem. Soc. 1971, 93, 2897.
15. Abdel-Magid, A.; Maryanoff, C. A.; Carson, K. G. Tetrahedron Lett. 1990, 31, 5595.
16. Layer, R. W. Chem. Rev. 1963, 63, 489-510.
17. Brown, C. A. Synthesis 1975, 326-327.
18. Gribble, G. W.; Nutaitis, C. F. Org. Prep. Proc. Int. 1985, 17, 317.
19. Tarbell, D. S.; Yamamoto, Y.; Pope, B. M. Proc. Nat. Acad. Sci. U.S.A. 1972, 69, 730-732.
20. Griffith, W. P.; Ley, S. V.; Whitcombe, G. P.; White, A. D. J. Chem, Soc., Chem Commun. 1987, 1625-1627.
21. Kyler, K. S.; Ghosal, S.; Luke, G. P. J. Org. Chem. 1987, 52, 4296-4298.
22. Oshima, K.; Kanemoto, S.; Matsubara, S.; Utimoto, K.; Nozaki, H. Chem. Lett. 1987, 5.
23. Liebeskind, L. S.; Feng, R. W. J. Org. Chem. 1990, 55, 5359-5364.
24. Liebeskind, L. S.; Riesinger, S. W. Tetrahedron Lett. 1991, 32, 5681-5682.
25. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.