Total synthesis of (+)-crocacin A

Tetrahedron Letters

Volumn 44, Issue 27, 2003, Pages 4989-4992

  Chakraborty, Tushar K ^a   Laxman, Pasunoori ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Aldol reaction; Antifungal; Crocacin; Cytotoxin; Enamide; Peterson olefination

Indexed keywords

ALKADIENE; AMIDE; ANTIFUNGAL AGENT; AZIDE; CROCACIN A; CYTOTOXIC AGENT; EPOXIDE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG POTENCY; DRUG SYNTHESIS; MOLECULE; STEREOCHEMISTRY;

EID: 0037842889     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01171-7     Document Type: Article

References (33)

1. Kunze B., Jansen R., Sasse F., Höfle G., Reichenbach H. J. Antibiot. 51:1998;1075-1080.
2. Jansen R., Washausen P., Kunze B., Reichenbach H., Höfle G. Eur. J. Org. Chem. 1999;1085-1089.
3. Kunze B., Jansen R., Höfle G., Reichenbach H. J. Antibiot. 47:1994;881-886.
4. Chakraborty T.K., Laxman P. Tetrahedron Lett. 43:2002;2645-2648.
5. Feutrill J.T., Lilly M.J., Rizzacasa M.A. Org. Lett. 4:2002;525-527.
6. Chakraborty T.K., Jayaprakash S., Laxman P. Tetrahedron. 57:2001;9461-9467.
7. Dias L.C., de Oliveira L.G. Org. Lett. 3:2001;3951-3954.
8. Chakraborty T.K., Jayaprakash S. Tetrahedron Lett. 42:2001;497-499.
9. Feutrill J.T., Lilly M.J., Rizzacasa M.A. Org. Lett. 2:2000;3365-3367.
10. Brown C.A., Ahuja V.K. J. Org. Chem. 38:1973;2226.
11. Brown C.A., Ahuja V.K. J. Chem. Soc., Chem. Commun. 1973;553.
12. For some useful references on skipped diynes and dienes, see: (a) Guiard, S.; Santelli, M.; Parrain, J.-L. Tetrahedron Lett. 2002, 43, 8099-8101. (b) Durand, S.; Parrain, J.-L.; Santelli, M. Synthesis 1998, 1015-1018. (c) Jeffery, T.; Gueugnot, S.; Linstrumelle, G. Tetrahedron Lett. 1992, 22, 5757-5760.
13. For some useful references on skipped diynes and dienes, see: (a) Guiard, S.; Santelli, M.; Parrain, J.-L. Tetrahedron Lett. 2002, 43, 8099-8101.
14. For some useful references on skipped diynes and dienes, see: (a) Guiard, S.; Santelli, M.; Parrain, J.-L. Tetrahedron Lett. 2002, 43, 8099-8101. (b) Durand, S.; Parrain, J.-L.; Santelli, M. Synthesis 1998, 1015-1018. (c) Jeffery, T.; Gueugnot, S.; Linstrumelle, G. Tetrahedron Lett. 1992, 22, 5757-5760.
15. For some useful references on skipped diynes and dienes, see: (a) Guiard, S.; Santelli, M.; Parrain, J.-L. Tetrahedron Lett. 2002, 43, 8099-8101. (b) Durand, S.; Parrain, J.-L.; Santelli, M. Synthesis 1998, 1015-1018. (c) Jeffery, T.; Gueugnot, S.; Linstrumelle, G. Tetrahedron Lett. 1992, 22, 5757-5760.
16. Chakraborty T.K., Reddy G.V. Tetrahedron Lett. 32:1991;679-682.
17. Chakraborty T.K., Reddy G.V. Tetrahedron Lett. 31:1990;1335-1338.
18. Tomoda S., Matsumoto Y., Takeuchi Y., Nomura Y. Bull. Chem. Soc. Jpn. 59:1986;3283-3284.
19. Tomoda S., Matsumoto Y., Takeuchi Y., Nomura Y. Chem. Lett. 1986;1193-1196.
20. Ager D.J. Org. React. 38:1990;1-223.
21. Ager D.J. Synthesis. 1984;384-398.
22. Hudrlick P.F., Peterson D., Rona R. J. Org. Chem. 40:1975;2263-2264.
23. Hudrlick P.F., Peterson D. J. Am. Chem. Soc. 97:1975;1464-1468.
24. For earlier work on the synthesis of enamides, see: (a) Fürstner, A.; Brehm, C.; Cancho-Grande, Y. Org. Lett. 2001, 3, 3955-3957; (b) Bhattacharjee, A.; Seguil, O. R.; De Brabander, J. K. Tetrahedron Lett. 2001, 42, 1217-1220; (c) Stefanuti, I.; Smith, S. A.; Taylor, R. J. K. Tetrahedron Lett. 2000, 41, 3735-3738; (d) Shen, R.; Porco, J. A., Jr. Org. Lett. 2000, 2, 1333-1336; (e) Snider, B. B.; Song, F. Org. Lett. 2000, 2, 407-408; (f) Kuramochi, K.; Watanabe, H.; Kitahara, T. Synlett 2000, 397-399; (g) Brettle, R.; Mosedal, A. J. J. Chem. Soc., Perkin Trans. 1 1988, 2185-2195; (h) Hudrlik, P. F.; Hudrlik, A. M.; Rona, R. J.; Misra, R. N.; Withers, G. P. J. Am. Chem. Soc. 1977, 99, 1993-1996.
25. For earlier work on the synthesis of enamides, see: (a) Fürstner, A.; Brehm, C.; Cancho-Grande, Y. Org. Lett. 2001, 3, 3955-3957; (b) Bhattacharjee, A.; Seguil, O. R.; De Brabander, J. K. Tetrahedron Lett. 2001, 42, 1217-1220; (c) Stefanuti, I.; Smith, S. A.; Taylor, R. J. K. Tetrahedron Lett. 2000, 41, 3735-3738; (d) Shen, R.; Porco, J. A., Jr. Org. Lett. 2000, 2, 1333-1336; (e) Snider, B. B.; Song, F. Org. Lett. 2000, 2, 407-408; (f) Kuramochi, K.; Watanabe, H.; Kitahara, T. Synlett 2000, 397-399; (g) Brettle, R.; Mosedal, A. J. J. Chem. Soc., Perkin Trans. 1 1988, 2185-2195; (h) Hudrlik, P. F.; Hudrlik, A. M.; Rona, R. J.; Misra, R. N.; Withers, G. P. J. Am. Chem. Soc. 1977, 99, 1993-1996.
26. For earlier work on the synthesis of enamides, see: (a) Fürstner, A.; Brehm, C.; Cancho-Grande, Y. Org. Lett. 2001, 3, 3955-3957; (b) Bhattacharjee, A.; Seguil, O. R.; De Brabander, J. K. Tetrahedron Lett. 2001, 42, 1217-1220; (c) Stefanuti, I.; Smith, S. A.; Taylor, R. J. K. Tetrahedron Lett. 2000, 41, 3735-3738; (d) Shen, R.; Porco, J. A., Jr. Org. Lett. 2000, 2, 1333-1336; (e) Snider, B. B.; Song, F. Org. Lett. 2000, 2, 407-408; (f) Kuramochi, K.; Watanabe, H.; Kitahara, T. Synlett 2000, 397-399; (g) Brettle, R.; Mosedal, A. J. J. Chem. Soc., Perkin Trans. 1 1988, 2185-2195; (h) Hudrlik, P. F.; Hudrlik, A. M.; Rona, R. J.; Misra, R. N.; Withers, G. P. J. Am. Chem. Soc. 1977, 99, 1993-1996.
27. For earlier work on the synthesis of enamides, see: (a) Fürstner, A.; Brehm, C.; Cancho-Grande, Y. Org. Lett. 2001, 3, 3955-3957; (b) Bhattacharjee, A.; Seguil, O. R.; De Brabander, J. K. Tetrahedron Lett. 2001, 42, 1217-1220; (c) Stefanuti, I.; Smith, S. A.; Taylor, R. J. K. Tetrahedron Lett. 2000, 41, 3735-3738; (d) Shen, R.; Porco, J. A., Jr. Org. Lett. 2000, 2, 1333-1336; (e) Snider, B. B.; Song, F. Org. Lett. 2000, 2, 407-408; (f) Kuramochi, K.; Watanabe, H.; Kitahara, T. Synlett 2000, 397-399; (g) Brettle, R.; Mosedal, A. J. J. Chem. Soc., Perkin Trans. 1 1988, 2185-2195; (h) Hudrlik, P. F.; Hudrlik, A. M.; Rona, R. J.; Misra, R. N.; Withers, G. P. J. Am. Chem. Soc. 1977, 99, 1993-1996.
28. For earlier work on the synthesis of enamides, see: (a) Fürstner, A.; Brehm, C.; Cancho-Grande, Y. Org. Lett. 2001, 3, 3955-3957; (b) Bhattacharjee, A.; Seguil, O. R.; De Brabander, J. K. Tetrahedron Lett. 2001, 42, 1217-1220; (c) Stefanuti, I.; Smith, S. A.; Taylor, R. J. K. Tetrahedron Lett. 2000, 41, 3735-3738; (d) Shen, R.; Porco, J. A., Jr. Org. Lett. 2000, 2, 1333-1336; (e) Snider, B. B.; Song, F. Org. Lett. 2000, 2, 407-408; (f) Kuramochi, K.; Watanabe, H.; Kitahara, T. Synlett 2000, 397-399; (g) Brettle, R.; Mosedal, A. J. J. Chem. Soc., Perkin Trans. 1 1988, 2185-2195; (h) Hudrlik, P. F.; Hudrlik, A. M.; Rona, R. J.; Misra, R. N.; Withers, G. P. J. Am. Chem. Soc. 1977, 99, 1993-1996.
29. For earlier work on the synthesis of enamides, see: (a) Fürstner, A.; Brehm, C.; Cancho-Grande, Y. Org. Lett. 2001, 3, 3955-3957; (b) Bhattacharjee, A.; Seguil, O. R.; De Brabander, J. K. Tetrahedron Lett. 2001, 42, 1217-1220; (c) Stefanuti, I.; Smith, S. A.; Taylor, R. J. K. Tetrahedron Lett. 2000, 41, 3735-3738; (d) Shen, R.; Porco, J. A., Jr. Org. Lett. 2000, 2, 1333-1336; (e) Snider, B. B.; Song, F. Org. Lett. 2000, 2, 407-408; (f) Kuramochi, K.; Watanabe, H.; Kitahara, T. Synlett 2000, 397-399; (g) Brettle, R.; Mosedal, A. J. J. Chem. Soc., Perkin Trans. 1 1988, 2185-2195; (h) Hudrlik, P. F.; Hudrlik, A. M.; Rona, R. J.; Misra, R. N.; Withers, G. P. J. Am. Chem. Soc. 1977, 99, 1993-1996.
30. For earlier work on the synthesis of enamides, see: (a) Fürstner, A.; Brehm, C.; Cancho-Grande, Y. Org. Lett. 2001, 3, 3955-3957; (b) Bhattacharjee, A.; Seguil, O. R.; De Brabander, J. K. Tetrahedron Lett. 2001, 42, 1217-1220; (c) Stefanuti, I.; Smith, S. A.; Taylor, R. J. K. Tetrahedron Lett. 2000, 41, 3735-3738; (d) Shen, R.; Porco, J. A., Jr. Org. Lett. 2000, 2, 1333-1336; (e) Snider, B. B.; Song, F. Org. Lett. 2000, 2, 407-408; (f) Kuramochi, K.; Watanabe, H.; Kitahara, T. Synlett 2000, 397-399; (g) Brettle, R.; Mosedal, A. J. J. Chem. Soc., Perkin Trans. 1 1988, 2185-2195; (h) Hudrlik, P. F.; Hudrlik, A. M.; Rona, R. J.; Misra, R. N.; Withers, G. P. J. Am. Chem. Soc. 1977, 99, 1993-1996.
31. For earlier work on the synthesis of enamides, see: (a) Fürstner, A.; Brehm, C.; Cancho-Grande, Y. Org. Lett. 2001, 3, 3955-3957; (b) Bhattacharjee, A.; Seguil, O. R.; De Brabander, J. K. Tetrahedron Lett. 2001, 42, 1217-1220; (c) Stefanuti, I.; Smith, S. A.; Taylor, R. J. K. Tetrahedron Lett. 2000, 41, 3735-3738; (d) Shen, R.; Porco, J. A., Jr. Org. Lett. 2000, 2, 1333-1336; (e) Snider, B. B.; Song, F. Org. Lett. 2000, 2, 407-408; (f) Kuramochi, K.; Watanabe, H.; Kitahara, T. Synlett 2000, 397-399; (g) Brettle, R.; Mosedal, A. J. J. Chem. Soc., Perkin Trans. 1 1988, 2185-2195; (h) Hudrlik, P. F.; Hudrlik, A. M.; Rona, R. J.; Misra, R. N.; Withers, G. P. J. Am. Chem. Soc. 1977, 99, 1993-1996.
32. ++H].
33. 1H NMR spectrum along with a large shift in the 10-NH chemical shift. This necessitated devising an alternate strategy to synthesize crocacin B 2, which will be reported in due course.