Studies towards total synthesis of borrelidin, regioselective methylation of bis-epoxides and structure determination

Tetrahedron Letters

Volumn 38, Issue 34, 1997, Pages 6079-6082

  Haddad, Nizar ^a   Brik, Ashraf ^a   Grishko, Michael ^a  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

BORRELIDIN;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030871393     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01372-5     Document Type: Article

References (19)

1. Presented in part at the 60th Annual Meeting of the Israel Chemical Society, February 1996, 108.
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3. (b) Hoffmann, R. W. Angew. Chem. Int. Ed. Engl. 1992, 31, 1124;
4. (c) Somers, P. K.; Wandless, T. J.; Schreiber, S. L. J. Am. Chem. Soc. 1991, 113, 8045;
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6. (e)Mori, K.; Kuwahara, S. Tetrahedron 1986, 42, 5539;
7. (f) Mori, K.; Kuwahara, S. Tetrahedron 1986, 42, 5545.
8. Haddad, N.; Ashraf, B.; Grishko, M. Tetrahedron Lett., accepted for publication.
9. (a) Hanson, R. Chem. Rev. 1991, 91, 437;
10. (b) Behrens, C. H.; Sharpless, K. B. J. Org. Chem. 1985, 50, 5696;
11. Sharpless, K. B.; Behrens, C. H.; Katsuki, T.; Lee, A. W. M.; Martin, V. S.; Takatani, M.; Viti, S. M.; Walker, F. J.; Woodard, S. S. Pure & Appl. Chem. 1983, 55, 589.
12. (a) Suzuki, T.; Saimoto, H.; Tomioka, H.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1982, 23, 3597;
13. (b) Matthews, R. S.; Mihelich, E. D.; McGowan, L. S.; Daniels, K. J. Org. Chem. 1983, 48, 409;
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15. Chong, J. M.; Cyr, D. R.; Mar, E. K. Tetrahedron Lett. 1987, 28, 5009.
16. Inghardt, T.; Frejd, T.; Magnusson, G. J. Org. Chem. 1988, 53, 4542.
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18. 3) of: diol 2: (-) 135.5, (+) 133.2, (-) 129.8, (-) 127.7, (-) 76.1, (-) 74.6, (+) 66.5, (+) 66.2, (+) 45.6, (+) 41.2, (+) 39.7, (-) 32.7, (-) 32.3, (-) 27.1, (-) 27.1, (-) 26.7, (-) 20.7, (-) 20.1, (+) 19.3, (-) 14.8, (-) 14.1; diol 10: (-) 135.7, (-) 135.6, (-) 129.8, (-) 127.7, (-) 74.5, (-) 72.1, (+) 68.5, (+) 66.5, (+) 45.2, (+) 41.4, (+) 41.0, (-) 38.8, (-) 32.4, (-) 27.6, (-) 27.4, (-) 26.9, (-) 21.3, (-) 21.0, (+) 20.3, (-) 14.9, (-) 10.6; diol 11: (-) 135.7, (-) 135.6, (+) 133.7, (-) 129.8, (-) 127.8, (-) 76.2, (-) 71.4, (+) 68.4, (+) 66.3, (+) 47.0, (+) 41.5, (+) 40.2, (-) 40.2, (-) 32.8, (-) 27.1, (-) 26.9, (-) 26.5, (-) 19.6, (-) 19.3, (+) 19.2, (-) 14.2, (-) 10.7; diol 12: (-) 135.6, (-) 135.5, (-)129.8, (-) 129.7, (+) 127.7, (-) 127.7, (-) 71.6, (-) 71.5, (+) 68.5, (+) 68.3, (+) 45.9, (+) 41.7, (+) 41.0, (-) 40.2, (-) 39.0, (-) 27.2, (-) 26.7, (-) 26.7, (-) 20.9, (-) 20.3, (+) 19.3, (-) 10.8, (-) 10.0; alcohol 14: (-) 135.5, (+) 133.1, (-) 129.8, (-) 129.6, (-) 129.5, (-) 127.7, (-) 127.6, (-) 76.0, (+) 66.1, (+) 60.4, (+) 45.5, (+) 39.9, (+) 34.8, (-) 32.6, (-) 30.3, (-) 27.1, (-) 26.9, (-) 19.8, (-) 19.7, (+) 19.3, (-) 14.1; alcohol 19: 135.6, 133.2, 130.0, 129.8, 129.5, 127.7, 127.6, 74.6, 66.4, 60.4, 44.2, 41.0, 34.1, 32.3, 30.5, 27.4, 26.8, 20.9, 20.9, 19.3, 14.9.
19. D value of these compounds as it was found in diols 2, 10, 11 and 12.