Total synthesis of the marine metabolite (-)-clavosolide D

Organic Letters

Volumn 10, Issue 8, 2008, Pages 1637-1640

  Seden, Peter T ^a   Charmant, Jonathan P H ^a   Willis, Christine L ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CLAVOSOLIDE D; MACROLIDE;

ANIMAL; ARTICLE; BIOLOGY; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SPONGE (PORIFERA); SYNTHESIS;

ANIMALS; CYCLIZATION; MACROLIDES; MARINE BIOLOGY; MODELS, MOLECULAR; PORIFERA;

EID: 44449129115     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800386d     Document Type: Article

References (29)

1. (a) Rao, M. R.; Faulkner, D. J. J. Nat. Prod. 2002, 65, 386.
2. (b) Erickson, K. L.; Gustafson, K. R.; Pannell, L. K.; Beutler, J. A.; Boyd, M. R. J. Nat. Prod. 2002, 65, 1303.
3. Barry, C. S.; Bushby, N.; Charmant, J. P. H.; Elsworth, J. D.; Harding, J. R.; Willis, C. L. Chem. Commun. 2005, 5097.
4. Further synthetic investigations on the originally proposed structure of clavosolide A include: (a) Chakraborty, T. K.; Reddy, V. R. Tetrahedron Lett. 2006, 47, 2099.
5. (b) Yakambram, P.; Puranik, V. G.; Gurjar, M. K. Tetrahedron Lett. 2006, 47, 3781.
6. (a) Son, J. B.; Kim, S. N.; Kim, N. Y.; Lee, D. H. Org. Lett. 2006, 8, 661 and 3411.
7. (b) Smith, A. B., III; Simov, V. Org. Lett. 2006, 8, 3315.
8. (c) Barry, C. S.; Elsworth, J. D.; Seden, P. T.; Bushby, N.; Harding, J. R.; Alder, R. W.; Willis, C. L. Org. Lett. 2006, 8, 3319.
9. (d) Chakraborty, T. K.; Reddy, V. R.; Chattopadhyay, A. K. Tetrahedron Lett. 2006, 47, 7435.
10. Son, J. B.; Hwang, M-H.; Lee, W.; Lee, D-H. Org. Lett. 2007, 9, 3897.
11. (a) Nokami, J.; Nomiyama, K.; Shafi, S. M.; Kataoka, K. Org. Lett. 2004, 6. 1261.
12. (b) Nokami, J.; Ohga, M.; Nakamoto. H.; Malsubara, T.; Hussain, I.; Kataoka, K. J. Am. Chem. Soc. 2001, 123, 9168.
13. Nicolaou, K. C.; Seitz, S. P.; Papahatjis, D. P. J. Am. Chem. Soc. 1983, 105, 2430.
14. Ratcliffe. A. J.; Fraser-Reid, B. J. Chem. Soc., Perkin Trans. 1 1990, 747.
15. Dakir, M.; Auhmani, A.; Itto, M. Y. A.; Mazoir, N.; Akssira, M.; Pierrot. M.; Benharref, A. Synth. Commun. 2004, 34, 2001.
16. (a) Brown, H. C.; Jadhav, P. K. J. Am. Chem. Soc. 1983, 105, 2092.
17. (b) Racherla, U. S.; Brown, H. C. J. Org. Chem. 1991, 56, 401.
18. (a) Hart, D. J.; Bennett, C. E. Org. Lett. 2003, 5, 1499.
19. (b) Bennett, C. E.; Figueroa, R.; Hart, D. J.; Yang, D. Heterocycles 2006, 70, 119.
20. Takai, K.; Tagashira, M.; Kuroda, T.; Oshima, K.; Utimoto. K.; Nozaki, H. J. Am. Chem. Soc. 1986, 108, 6048.
21. (b) Jin, H.; Uenishi, J.; Christ, W. J.; Kishi, Y. J. Am. Chem. Soc. 1986, 108, 5644.
22. Hanessian, S.; Giroux, S.; Larsson, A. Org. Lett. 2006, 8, 5481.
23. Chan, T. H.; Li, C. J.; Lee, M. C.; Wei, Z. Y. Can. J. Chem. 1994, 72. 1181.
24. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512.
25. Mitsunobu, O.; Yamada. M. Bull. Chem. Soc. Jpn. 1967, 40. 2380.
26. Denmark, S. E.; Edwards, J. P. J. Org. Chem. 1991, 56, 6974.
27. Paterson, I.; Yeung, K. S.; Ward, R. A.; Smith, J. D.; Cumming, J. G.; Lamboley, S. Tetrahedron, 1995, 51, 9467.
28. Bavetsias, V.; Bisset, G. M. F.; Jarman, M. Synth, Commun. 1995, 25, 947.
29. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989.