Total synthesis and revision of C6 stereochemistry of (+)-amphidinolide W

Journal of Organic Chemistry

Volumn 71, Issue 3, 2006, Pages 1085-1093

  Ghosh, Arun K ^a   Gong, Gangli ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CATALYSIS; ENZYMES; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

AMPHIDINOLIDE W; C6 STEREOCHEMISTRY; METATHESIS; YAMAGUCHI MACROLACTONIZATION REACTION;

ORGANIC COMPOUNDS;

ACETIC ACID; AMPHIDINOLIDE W; CYTOTOXIC AGENT; MACROCYCLIC COMPOUND; NATURAL PRODUCT; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DIHYDROXYLATION; HYDROLYSIS; INFRARED SPECTROSCOPY; MACROLACTONIZATION; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; RING CLOSING METATHESIS; STEREOCHEMISTRY; SYNTHESIS;

BUTYRIC ACIDS; LACTONES; MACROLIDES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NITRO COMPOUNDS; STEREOISOMERISM;

EID: 32144460995     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052181z     Document Type: Article

References (48)

1. Kobayashi, J.; Shimbo, K.; Kubota, T.; Tsuda, M. Pure Appl. Chem. 2003, 75, 337.
2. Kobayashi, J.; Tsuda, M. Nat. Prod. Rep. 2004, 21, 77.
3. (a) Lam, H. W.; Pattenden, G. Angew. Chem., Int. Ed. 2002, 41, 508.
4. (b) Maleczka, R. E.; Terrell, L. R.; Geng, F.; Ward, J. S. Org. Lett. 2002, 4, 2841.
5. (c) Trost, B. M.; Chisholm, J. D.; Wrobleski, S. T.; Jung, M. J. Am. Chem. Soc. 2002, 124, 12420.
6. (d) Trost, B. M.; Harrington, P. E. J. Am. Chem. Soc. 2004, 126, 5028.
7. (a) Williams, D. R.; Kissel, W. S. J. Am. Chem. Soc. 1998, 120, 11198.
8. (b) Williams, D. R.; Meyer, K. G. J. Am. Chem. Soc. 2001, 123, 765.
9. (c) Williams, D. R.; Myers, B. J.; Mi, L. Org. Lett. 2000, 2, 945.
10. (d) Trost, B. M.; Papillon, J. P. N. J. Am. Chem. Soc. 2004, 126, 13618.
11. (a) Ghosh, A. K.; Liu, C. J. Am. Chem. Soc. 2003, 125, 2374.
12. (b) Furstner, A.; Aissa, C.; Riveiros, R.; Ragot, J. Angew. Chem., Int. Ed. 2002, 41, 4763.
13. (c) Aiessa, C.; Riveiros, R.; Ragot, J.; Fuerstner, A. J. Am. Chem. Soc. 2003, 125, 15512.
14. (d) Colby, E. A.; O'Brien, K.; Jamison, T. F. J. Am. Chem. Soc. 2004, 126, 998.
15. (e) Lepage, O.; Kattnig, E.; Fuerstner, A. J. Am. Chem. Soc. 2004, 126, 15970.
16. (f) Colby, E. A.; O'Brien, K. C.; Jamison, T. F. J. Am. Chem. Soc. 2005, 127, 4297.
17. Shimbo, K.; Tsuda, M.; Izui, N.; Kobayashi, J. J. Org. Chem. 2002, 67, 1020.
18. Ghosh, A. K.; Gong, G. J. Am. Chem. Soc. 2004, 126, 3704.
19. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
20. (a) Horner, L.; Hoffmann, H.; Wippel, J. H. G.; Klahre, G. Ber. 1959, 92, 2499.
21. (b) Wadsworth, W. S., Jr.; Emmons, W. D. J. Am. Chem. Soc. 1961, 83, 1733.
22. Evans, D. A.; Ennis, M. D.; Mathre, D. J. J. Am. Chem. Soc. 1982, 104, 1737.
23. Baillie, L.; Batsanov, A.; Bearder, J.; Whiting, D. J. Chem. Soc., Perkin Trans, 1 1998, 20, 3471.
24. Evans, P. A.; Murthy, V. S. Tetrahedron Lett. 1999, 40, 1253.
25. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
26. Hayashi, H.; Nakanishi, K.; Brandon, C.; Marmur J. Am. Chem. Soc. 1973, 95, 8749.
27. Rivero, R. A.; Greenlee, W. S. Tetrahedron Lett. 1991, 32, 2453.
28. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815.
29. Ishiwata, A.; Sakamoto, S.; Noda, T.; Hirama, M. Synlett 1999, 6, 692.
30. Paterson, I.; Yeung, K.; Watson, C.; Ward, R. A.; Wallace, P. A. Tetrahedron 1998, 54, 11935.
31. For a general reaction protocol, see: Semmelhack, M. F.; Stauffer, R. D.; Yamashita, A. J. Org. Chem. 1977, 42, 3180.
32. (a) Furstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012.
33. (b) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446.
34. (c) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
35. (d) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073.
36. For the effect of Lewis acid on RCM, see: (a) Ghosh, A. K.; Cappiello, J.; Shin, D. Tetrahedron Lett. 1998, 39, 4651.
37. (b) Ghosh, A. K.; Bilcer, G. Tetrahedron Lett. 2000, 41, 1003.
38. Scholl, M.; Ding, S.; Lee, C.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
39. (a) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
40. (b) Blackwell, H. E.; O'Leary, D. J.; Chatterjee, A. K.; Washenfelder, R. A.; Bussmann, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 58.
41. (c) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783.
42. (d) Chatterjee, A. K.; Choi, T.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360.
43. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989.
44. Caserio, F. F., Jr.; Roberts, J. D. J. Am. Chem. Soc. 1958, 80, 5837.
45. (a) Ghosh, A. K.; Chen, Y. Tetrahedron Lett. 1995, 36, 505.
46. (b) Ghosh, A. K.; Kincaid, J. F.; Walters, D. E.; Chen, Y.; Chaudhuri, N. C.; Thompson, W. J.; Culberson, C.; Fitzgerald, P. M. D.; Lee, H. Y.; McKee, S. P.; Munson, P. M.; Duong, T. T.; Darke, P. L.; Zugay, J. A.; Schleif, W. A.; Axel, M. G.; Lin, J.; Huff, J. R. J. Med. Chem. 1996, 39, 3278.
47. Borden, E. P.; Keck, G. E. J. Org. Chem. 1985, 50, 2394.
48. Trost, B. M.; Chisholm, J. D. Org. Lett. 2002, 4, 3743.