Total synthesis of dolabelide D

Journal of the American Chemical Society

Volumn 128, Issue 9, 2006, Pages 2796-2797

  Park, Peter K ^a   O'Malley, Steven J ^a   Schmidt, Darby R ^a   Leighton, James L ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; DOLABELIDE D; MACROLIDE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; DEPROTECTION REACTION; DRUG CYTOTOXICITY; DRUG SYNTHESIS; ESTERIFICATION; OXIDATION; QUANTUM YIELD; RING CLOSING METATHESIS; STEREOSPECIFICITY;

ANIMALS; DITERPENES; MOLLUSCA; SILANES;

EID: 33644935442     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja058692k     Document Type: Article

References (21)

1. Ojika, M.; Nagoya, T.; Yamada, K. Tetrahedron Lett. 1995, 36, 7491.
2. Suenaga, K.; Nagoya, T.; Shibata, T.; Kigoshi, H.; Yamada, K. J. Nat. Prod. 1997, 60, 155.
3. (a) Grimaud, L.; de Mesmay, R.; Prunet, J. Org. Lett. 2002, 4, 419.
4. (b) Desroy, N.; Le Roux, R.; Phansavath, P.; Chiummiento, L.; Bonini, C.; Genêt, J.-P. Tetrahedron Lett. 2003, 44, 1763.
5. (c) Le Roux, R.; Desroy, N.; Phansavath, P.; Genêt, J.-P. Synlett 2005, 429.
6. (d) Keck, G. E.; McLaws, M. D. Tetrahedron Lett. 2005, 46, 4911.
7. Schmidt, D. R.; Park, P. K.; Leighton, J. L. Org. Lett. 2003, 5, 3535.
8. Schmidt, D. R.; O'Malley, S. J.; Leighton, J. L. J. Am. Chem. Soc. 2003, 125, 1190.
9. (a) Zacuto, M. J.; O'Malley, S. J.; Leighton, J. L. J. Am. Chem. Soc. 2002, 124, 7890.
10. (b) Zacuto, M. J.; O'Malley, S. J.; Leighton, J. L. Tetrahedron 2003, 59, 8889.
11. Taguchi, H.; Ghoroku, K.; Tadaki, M.; Tsubouchi, A.; Takeda, T. Org. Lett. 2001, 3, 3811.
12. (a) Paterson, I.; Goodman, J. M.; Lister, M. A.; Schumann, R. C.; McClure, C. K.; Norcross, R. D. Tetrahedron 1990, 46, 4663.
13. (b) Paterson, I.; Florence, G. J.; Gerlach, K.; Scott, J. P.; Sereinig, N. J. Am. Chem. Soc. 2001, 123, 9535.
14. Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560.
15. For a discussion of the advantages of this diol-protecting group, see: Evans, D. A.; Connell, B. T. J. Am. Chem. Soc. 2003, 125, 10899.
16. Kubota, K.; Leighton, J. L. Angew. Chem., Int. Ed. 2003, 42, 946.
17. Hackman, B. M.; Lombardi, P. J.; Leighton, J. L. Org. Lett. 2004, 6, 4375.
18. Still, W. C.; Barrish, J. C. J. Am. Chem. Soc. 1983, 105, 2487.
19. (a) Paterson, I.; Gibson, K. R.; Oballa, R. M. Tetrahedron Lett. 1996, 37. 8585.
20. (b) Evans, D. A.; Coleman, P. J.; Côté. B. J. Org. Chem. 1997, 62, 788.
21. The recently reported method to suppress such pathways did not provide significant improvement in this case. See: Hong, S. H.; Sanders, D. P.; Lee, C. W.; Grubbs, R. H. J. Am. Chem. Soc. 2005, 127, 17160.