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Volumn 4, Issue 6, 2002, Pages 897-900

A biosynthetic proposal for ring formation in the antitumor agent halichomycin. Asymmetric synthesis of the AB-carbon backbone of halichomycin

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CARBON; FUSED HETEROCYCLIC RINGS; HALICHOMYCIN;

EID: 0037149686     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol017266a     Document Type: Article
Times cited : (14)

References (23)
  • 2
    • 0003787433 scopus 로고    scopus 로고
    • Barton D., Nakanishi, K., Meth-Cohn, O., Eds.; Pergamon: Oxford, Chapter 8.07
    • Kobayashi, J.; Ishibashi, M. Comprehensive Natural Product Chemistry; Barton D., Nakanishi, K., Meth-Cohn, O., Eds.; Pergamon: Oxford, 1999; Vol. 8, Chapter 8.07, p 416.
    • (1999) Comprehensive Natural Product Chemistry , vol.8 , pp. 416
    • Kobayashi, J.1    Ishibashi, M.2
  • 3
    • 0000921762 scopus 로고
    • It is well-known that primary amides add reversibly to the carbonyl group of aldehydes and ketones in acidic, neutral, or basic media. In fact, for many aldehydes, the resulting N-acylcarbinolamines are quite stable and isolable. According to Weinreb, the equilibria of such additions usually lies toward the N-acylcarbinolamine to the extent of 5 kcal/mol. See: Auerbach, J.; Zamore, M.; Weinreb, S. M. J. Org. Chem. 1976, 41, 725.
    • (1976) J. Org. Chem. , vol.41 , pp. 725
    • Auerbach, J.1    Zamore, M.2    Weinreb, S.M.3
  • 4
    • 0000325030 scopus 로고
    • Barton, D., Ollis, W. D., Eds.; Pergamon: Oxford, Chapter 9.9
    • For reviews on this topic, see: (a) Challis, B. C.; Challis, J. A. Comprenensive Organic Chemistry; Barton, D., Ollis, W. D., Eds.; Pergamon: Oxford, 1979; Vol. 2, Chapter 9.9, p 957.
    • (1979) Comprenensive Organic Chemistry , vol.2 , pp. 957
    • Challis, B.C.1    Challis, J.A.2
  • 9
    • 0002976361 scopus 로고
    • The addition of alcohols to N-acylimines derived from N-acylcarbinolamines is well precedented in the chemical literature. See: Zaugg, H. E.; Martin, W. B. Org. React. 1965, 14, 52.
    • (1965) Org. React. , vol.14 , pp. 52
    • Zaugg, H.E.1    Martin, W.B.2
  • 22
    • 0031032857 scopus 로고    scopus 로고
    • For an alternative synthetic strategy to the C(1)-C(7)-segment of halichomycin which also utilises ylide 11, see: McGann, E. E.; Janes, G.; Ortsey, C.; Wood, J. L. Tetrahedron Lett. 1997, 38, 303.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 303
    • McGann, E.E.1    Janes, G.2    Ortsey, C.3    Wood, J.L.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.