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Volumn 44, Issue 43, 2003, Pages 7901-7904

Organocatalytic Michael addition, a convenient tool in total synthesis. First asymmetric synthesis of (-)-botryodiplodin

Author keywords

[No Author keywords available]

Indexed keywords

(3 NITROBUT 2 ENYLOXYMETHYL)BENZENE; ANTIBIOTIC AGENT; BENZENE DERIVATIVE; DIAMINE; KETONE; PROPIONALDEHYDE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0141425514     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.017     Document Type: Article
Times cited : (92)

References (29)
  • 8
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    • iPBP, under the same conditions, we have now obtained the adduct with 93% ee and 95:5 dr instead of 83% ee and 95:5 dr (Ref. 4a). New experiments have revealed a problem with the optical purity of some crops of our chiral diamine, which was only 89% ee. With an optically pure diamine
    • New experiments have revealed a problem with the optical purity of some crops of our chiral diamine, which was only 89% ee. With an optically pure diamine iPBP , under the same conditions, we have now obtained the adduct with 93% ee and 95:5 dr instead of 83% ee and 95:5 dr (Ref. 4a).
  • 9
    • 85031056332 scopus 로고    scopus 로고
    • For other syntheses of racemic botryodiplodin see: (a) McMurry, P. M. J. ; Abe, K. J. Am. Chem. Soc. 1973, 95, 5824; (b) McMurry, P. M. J.; Abe, K. Tetrahedron Lett. 1973, 14, 4103; (c) Mukaiyama, T.; Wada, M.; Hanna, J. Chem. Lett. 1974, 94, 1181; (d) Wilson, S. R.; Myers, R. S. J. Org. Chem. 1975, 40, 3309; (e) Kurth, M. J.; Yu, C.-M. J. Org. Chem. 1985, 50, 1840. (f) Dulcere, J. P.; Mihoubi, M. N.; Rodriguez, J. J. Org. Chem. 1993, 58, 5709; (g) Daub, G. W. ; Edwards, J. P.; Okada, C. R.; Allen, J. W.; Maxey, C. T.; Wells, M. S.; Goldstein, A. S.; Dibley, M. J.; Wang, C. J.; Ostercamp, D. P.; Chung, S.; Cunningham, P. S.; Berliner, M. A. J. Org. Chem. 1997, 62, 1976; (h) Nouguier, R.; Gastaldi, S.; Stien, D.; Bertrand, M.; Renaud, P. Tetrahedron Lett. 1999, 40, 3371; (i) Villar, F.; Andrey, O.; Renaud, P. Tetrahedron Lett. 1999, 40, 3375.
    • For other syntheses of racemic botryodiplodin see: (a) McMurry, P. M. J. ; Abe, K. J. Am. Chem. Soc. 1973, 95, 5824; (b) McMurry, P. M. J.; Abe, K. Tetrahedron Lett. 1973, 14, 4103; (c) Mukaiyama, T.; Wada, M.; Hanna, J. Chem. Lett. 1974, 94, 1181; (d) Wilson, S. R.; Myers, R. S. J. Org. Chem. 1975, 40, 3309; (e) Kurth, M. J.; Yu, C.-M. J. Org. Chem. 1985, 50, 1840. (f) Dulcere, J. P.; Mihoubi, M. N.; Rodriguez, J. J. Org. Chem. 1993, 58, 5709; (g) Daub, G. W. ; Edwards, J. P.; Okada, C. R.; Allen, J. W.; Maxey, C. T.; Wells, M. S.; Goldstein, A. S.; Dibley, M. J.; Wang, C. J.; Ostercamp, D. P.; Chung, S.; Cunningham, P. S.; Berliner, M. A. J. Org. Chem. 1997, 62, 1976; (h) Nouguier, R.; Gastaldi, S.; Stien, D.; Bertrand, M.; Renaud, P. Tetrahedron Lett. 1999, 40, 3371; (i) Villar, F.; Andrey, O.; Renaud, P. Tetrahedron Lett. 1999, 40, 3375.
  • 21
    • 0000851805 scopus 로고
    • The Henry (nitroaldol) Reaction
    • B.M. Trost, & I. Fleming. Oxford: Pergamon Press
    • Rosini G. The Henry (nitroaldol) Reaction. Trost B.M., Fleming I. Comprehensive Organic Synthesis. 2:1991;321-340 Pergamon Press, Oxford.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 321-340
    • Rosini, G.1
  • 26
    • 0000125222 scopus 로고    scopus 로고
    • 4OAc: McMurry, J. E.; Melton, J.; Padgett, H. J. Org. Chem. 1974, 39, 259.
  • 27
    • 85031055062 scopus 로고    scopus 로고
    • t (10-anti): 5.2, 5.6 min.
    • t ( 10-anti ): 5.2, 5.6 min.
  • 28
    • 85031053491 scopus 로고    scopus 로고
    • t (1β): 48.2 min
    • t ( 1β ): 48. 2 min.
  • 29
    • 85031059046 scopus 로고    scopus 로고
    • note
    • t ( 12β ): 38.7, 39.3 min.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.