Total synthesis of (+)-allocyathin B2

Journal of the American Chemical Society

Volumn 127, Issue 9, 2005, Pages 2844-2845

  Trost, Barry M ^a   Dong, Li ^a   Schroeder, Gretchen M ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 METHYLCYCLOPENTANONE; ALKENE; ALLOCYATHIN; CYCLOPENTANONE DERIVATIVE; PALLADIUM; TERPENOID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; DRUG SYNTHESIS; ENANTIOSELECTIVITY; GLYCOSIDATION; KNOEVENAGEL CONDENSATION;

ALKYLATION; CYCLIZATION; DITERPENES; PALLADIUM; POLYCYCLIC COMPOUNDS;

EID: 14844298623     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0435586     Document Type: Article

References (35)

1. (a) Ayer, W. A.; Lee, S. P. Can. J. Chem. 1979, 57, 3332-3337.
2. (b) Allbutt, A. D.; Ayer, W. A.; Brodie, H. J.; Johri, B. N.; Taube, H. Can. J. Microbiol. 1971, 17, 1401-1402.
3. (c) Ayer, W. A.; Taube, H. Tetrahedron Lett. 1972, 13, 1917-1920.
4. (d) Ayer, W. A.; Taube, H. Can. J. Chem. 1973, 51, 3842-3843.
5. (e) Ayer, W. A.; Browne, L. M.; Mercer, J. R.; Taylor, D. R.; Ward, D. E. Can. J. Chem. 1978, 56, 717-721.
6. (f) Ayer, W. A.; Yoshida, T.; Van Schie, D. M. J. Can. J. Chem. 1978, 56, 2113-2120.
7. (g) Ayer, W. A.; Lee, S. P.; Nakashima, T. T. Can. J. Chem. 1979, 57, 3338-3343.
8. (h) Ayer, W. A.; Browne, L. M. Tetrahedron 1981, 37, 2199-2248.
9. Kawagishi, H.; Shimada, A.; Shirai, R.; Okamoto, K.; Ojima, F.; Sakamoto, H.; Ishiguro, Y.; Furukawa, S. Tetrahedron Lett. 1994, 35, 1569-1572.
10. Synthesis of cyathin core: (a) Wright, D. L.; Whitehead, C. R. Org. Prep. Proced. Int. 2000, 32, 307-320. (b) Wender, P. A.; Bi, F. C.; Brodney, M. A.; Gosselin, F. Org. Lett. 2001, 3, 2105-2108. (c) Tekeda, K.; Nakane, D.; Tekeda, M. Org. Lett. 2000, 2, 1903-1905. (d) Thominiaux, C.; Chiaroni, A.; Desmaele, D. Tetrahedron Lett. 2002, 43, 4107-4110.
11. Synthesis of cyathin core: (a) Wright, D. L.; Whitehead, C. R. Org. Prep. Proced. Int. 2000, 32, 307-320. (b) Wender, P. A.; Bi, F. C.; Brodney, M. A.; Gosselin, F. Org. Lett. 2001, 3, 2105-2108. (c) Tekeda, K.; Nakane, D.; Tekeda, M. Org. Lett. 2000, 2, 1903-1905. (d) Thominiaux, C.; Chiaroni, A.; Desmaele, D. Tetrahedron Lett. 2002, 43, 4107-4110.
12. Synthesis of cyathin core: (a) Wright, D. L.; Whitehead, C. R. Org. Prep. Proced. Int. 2000, 32, 307-320. (b) Wender, P. A.; Bi, F. C.; Brodney, M. A.; Gosselin, F. Org. Lett. 2001, 3, 2105-2108. (c) Tekeda, K.; Nakane, D.; Tekeda, M. Org. Lett. 2000, 2, 1903-1905. (d) Thominiaux, C.; Chiaroni, A.; Desmaele, D. Tetrahedron Lett. 2002, 43, 4107-4110.
13. Synthesis of cyathin core: (a) Wright, D. L.; Whitehead, C. R. Org. Prep. Proced. Int. 2000, 32, 307-320. (b) Wender, P. A.; Bi, F. C.; Brodney, M. A.; Gosselin, F. Org. Lett. 2001, 3, 2105-2108. (c) Tekeda, K.; Nakane, D.; Tekeda, M. Org. Lett. 2000, 2, 1903-1905. (d) Thominiaux, C.; Chiaroni, A.; Desmaele, D. Tetrahedron Lett. 2002, 43, 4107-4110.
14. (a) Tori, M.; Toyoda, N.; Sono, M. J. Org. Chem. 1998, 63, 306-313.
15. (b) Snider, B. B.; Vo, N. H.; O'Neil, S. V. J. Org. Chem. 1998, 63, 4732-4340.
16. 2 by resolution.
17. (a) Trost, B. M.; Schroeder, G. M. J. Am. Chem. Soc. 1999, 121, 6759-6760.
18. (b) Trost, B. M.; Schroeder, G. M.; Kristensen, J. Angew. Chem., Int. Ed. 2002, 41, 3492-3495.
19. Trost, B. M.; Pissot-Soldermann, C.; Chen, I.; Schroeder, G. M. J. Am. Chem. Soc. 2004, 126, 4480-4481.
20. McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1983, 24, 979-982.
21. Corey, E. J.; Kang, M.; Desai, M. C.; Ghosh, A. K.; Houpis, I. N. J. Am. Chem. Soc. 1988, 110, 649-651.
22. Nesnas, N.; Rando, R. R.; Nakanishi, K. Tetrahedron 2002, 58, 6577-6584.
23. (a) Negishi, E.; Valente, L. F.; Kobayashi, M. J. Am. Chem. Soc. 1980, 102, 3298-3299.
24. (b) Negishi, E.; Swanson, D. R.; Rousset, C. J. J. Org. Chem. 1990, 55, 5406-5409.
25. (a) Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067-2096.
26. (b) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 714-715.
27. (c) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 9728-9729.
28. (d) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2002, 124, 5025-5036.
29. The relative stereochemistry was established by comparison with the cis series, which was prepared independently and will be reported in due course.
30. For complete double bond isomerization in the formation of seven-membered rings from 1,7-enynes, see refs 11b and 11d.
31. (a) Ono, T.; Tamaoka, T.; Yuasa, Y.; Matsuda, T.; Nokami, J.; Wakabayashi, S. J. Am. Chem. Soc. 1984, 106, 7890-7893.
32. (b) Nokami, J.; Mandai, T.; Imakura, Y.; Nishiuchi, K.; Kawada, M.; Wakabayashi, S. Tetrahedron Lett. 1981, 22, 4489-4490.
33. (c) Trost, B. M.; Mallert, S. Tetrahedron Lett. 1993, 34, 8025-8028.
34. The relative stereochemistry of the C14 oxygen-bearing stereocenter was assigned by comparison of the final product with the natural material.
35. Ho, P.-T. Tetrahedron Lett. 1978, 19, 1623-1626.