Total synthesis of (+)-crocacin C

Organic Letters

Volumn 3, Issue 24, 2001, Pages 3951-3953

  Dias, Luiz C ^a   De Oliveira, Luciana G ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

CROCACIN; POLYENE;

ARTICLE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

POLYENES; STEREOISOMERISM; SUPPORT, NON-U.S. GOV'T;

EID: 0035969625     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016845c     Document Type: Article

References (33)

1. Kunze, B.; Jansen, R.; Hofle, G.; Reichenbach, H. J. Antibiot. 1994, 47, 881.
2. (a) Jansen, R.; Washausen, P.; Kunze, B.; Reichennach, H.; Hofle. G. Eur. J. Org. Chem. 1999, 1085.
3. (b) Kunze, B.; Jansen, R.; Sasse, F.; Hofle, G.; Reichenbach, H. J. Antibiot. 1998, 51, 1075.
4. As this work was in progress, the first two asymmetric total syntheses of crocacin C were described: (a) Feutrill, J. T.; Lilly, M. J.; Rizzacasa, M. A. Org. Lett. 2000, 2, 3365.
5. (b) Chakraborty, T. K.; Jayaprakash, S. Tetrahedron Lett. 2001, 42, 497.
6. The numbering of 3 follows that suggested in ref 2a.
7. Evans, D. A.; Gage, J. R. Org. Synth. 1989, 68, 83.
8. (a) Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127.
9. (b) Evans, D. A.; Taber, T. R. Tetrahedron Lett. 1980, 21, 4675.
10. (c) Evans, D. A.; Ng, H. P.; Clark, J. S.; Rieger, D. L. Tetrahedron 1992, 48, 2127.
11. Levin, J. I.; Turos, E.; Weinreb, S. Synth. Commun. 1982, 12, 989.
12. Mancuso, A. J.; Swern, D. Synthesis 1981, 165.
13. Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863.
14. (a) Isobe, M.; Kitamura, M.; Mio, S.; Goto, T. Tetrahedron Lett. 1982, 23, 221.
15. (b) Maruyama, K.; Ueda, M.; Sasaki, S.; Iwata, Y.; Miyazawa, M.; Miyashita, M. Tetrahedron Lett. 1998, 39, 4517.
16. Johnson, M. R.; Kishi, Y. Tetrahedron Lett. 1979, 20, 4347.
17. (a) Rychnovsky, S. D.; Skalitzky, D. J. Tetrahedron Lett. 1990, 31, 945.
18. (b) Evans, D. A.; Rieger, D. L.; Gage, J. R. Tetrahedron Lett. 1990, 31, 7099.
19. (c) Rychnovsky, S. D.; Rogers, B. N.; Richardson, T. I. Acc. Chem. Res. 1998, 31, 9.
20. Diols 16 and 17 showed spectral data and physical properties identical in all respects with published data. See ref 3.
21. (a) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
22. (b) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 49, 4155.
23. (c) Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
24. (a) Takai, K.; Nitta, K.; Utimoto, K. J. Am. Chem. Soc. 1986, 108, 7408.
25. (b) Paterson, I.; Lombart, H.; Allerton, C. M. N. Org. Lett. 1999, 1, 19.
26. Piers, E.; Morion, H. E. J. Org. Chem. 1980, 45, 4263.
27. Brabander, J. D.; Vandewalle, M. Synthesis 1994, 855.
28. (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
29. (b) Duncton, A. J.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1999, 1235.
30. (c) Stille, J. K.; Groh, B. L. J. Am. Chem. Soc. 1987, 109, 813.
31. (a) Farina, V. Pure Appl. Chem. 1996, 68, 73.
32. (b) Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585.
33. 13C NMR, IR, HRMS, and analytical data. Yields refer to chromatographically and spectroscopically homogeneous materials.