Synthesis of the pentacyclic xestobergsterol skeleton

Tetrahedron

Volumn 54, Issue 25, 1998, Pages 7033-7044

  Krafft, Marie E ^a   Dasse, Olivier A ^a   Shao, Bin ^a  

^a FLORIDA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HISTAMINE RELEASE INHIBITOR; UNCLASSIFIED DRUG; XESTOBERGOSTEROL;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 0032543737     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00345-7     Document Type: Article

References (15)

1. 1. Shoji, N.; Umeyama, A.; Shin, K.; Takeda, K.; Arihara, S. J. Org. Chem. 1992, 57, 2996.
2. 2. The isolation and identification of xestobergsterol-C [2-β-hydroxy-xestobergsterol-A] has been reported: Kobayashi, J.; Shinonaga, H.; Shigemori, H.; Uneyama, A.; Shoji, N. Arihara, S. J. Nat. Prod. 1995, 58, 312. The original structure of xestobergsterol-A was revised (C-23) as a result of structural information generated during the identification of xestobergsterol-C.
3. 3 Takei, M.; Umeyama, A.; Shoji, N.; Arihara, S.; Endo, K. Experientia, 1993, 49, 145.
4. 4. Pauson, P. L. Tetrahedron 1985, 41, 5855. Schore, N. E. Org. React. 1991, 40, 1. Schore, N. E. in 'Comprehensive Organic Synthesis', Volume 5, Ed. B. M. Trost, Pergamon: Oxford, 1991, p. 1037. N. E. Schore In Comprehensive Organometallic Chemistry-II; Hegedus, L. S., Ed.; Pergamon: Oxford, 1995; Vol. 12, p 703.
5. 4. Pauson, P. L. Tetrahedron 1985, 41, 5855. Schore, N. E. Org. React. 1991, 40, 1. Schore, N. E. in 'Comprehensive Organic Synthesis', Volume 5, Ed. B. M. Trost, Pergamon: Oxford, 1991, p. 1037. N. E. Schore In Comprehensive Organometallic Chemistry-II; Hegedus, L. S., Ed.; Pergamon: Oxford, 1995; Vol. 12, p 703.
6. 4. Pauson, P. L. Tetrahedron 1985, 41, 5855. Schore, N. E. Org. React. 1991, 40, 1. Schore, N. E. in 'Comprehensive Organic Synthesis', Volume 5, Ed. B. M. Trost, Pergamon: Oxford, 1991, p. 1037. N. E. Schore In Comprehensive Organometallic Chemistry-II; Hegedus, L. S., Ed.; Pergamon: Oxford, 1995; Vol. 12, p 703.
7. 4. Pauson, P. L. Tetrahedron 1985, 41, 5855. Schore, N. E. Org. React. 1991, 40, 1. Schore, N. E. in 'Comprehensive Organic Synthesis', Volume 5, Ed. B. M. Trost, Pergamon: Oxford, 1991, p. 1037. N. E. Schore In Comprehensive Organometallic Chemistry-II; Hegedus, L. S., Ed.; Pergamon: Oxford, 1995; Vol. 12, p 703.
8. 5. Krafft, M. E.; Chirico, X. Tetrahedron Lett. 1994, 35, 4511.
9. 6. Cleve, A.; Neef, G.; Ottow, E.; Scholz, S.; Schwede, W. Tetrahedron, 1995, 51, 5563.
10. 7. Crabbe, P.; Cruz, A.; Iriarte, J. Can. J. Chem. 1968, 46, 349.
11. 8. Johnson, W. S.; Johns, W. F. J. Am. Chem. Soc. 1957, 79, 2005.
12. 9. Takahashi, T.; Ootake, A.; Tsuji, J. Tetrahedron, 1995, 41, 5747.
13. 10. Proton NOE difference experiments were used to verify the relative configuration of the C-15 carbinol center and the newly formed C-17 stereogenic center.
14. 11. Krafft, M. E.; Wilson, A. M.; Dasse, O. A.; Cheung, Y. Y.; Shao, B.; Fu, Z.; Bonaga, L. V. R.; Mollman, M. K. J. Am. Chem. Soc. 1996, 18, 6080.
15. 12. Jung has recently reported the synthesis of 7-Deoxyxestobergsterol A: Jung, M. E.; Johnson, T. W. J. Am. Chem. Soc. 1997, 119, 12412.