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Volumn 10, Issue 2, 1999, Pages 297-306

Formal enantioselective synthesis of (+)-vincamine. The first enantioselective route to (+)-3,14-epivincamine and its enantiomer

Author keywords

[No Author keywords available]

Indexed keywords

2 ETHYL 2 (2 METHOXYCARBONYLETHYL)CYCLOPENTANONE; 2 ETHYLCYCLOPENTANONE; 3,14 EPIVINCAMINE; ACRYLIC ACID METHYL ESTER; ALPHA METHYLBENZYLAMINE; UNCLASSIFIED DRUG; VINCAMINE;

EID: 0033613890     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00489-3     Document Type: Article
Times cited : (18)

References (24)
  • 7
    • 0030972990 scopus 로고    scopus 로고
    • For the most recent enantioselective total synthesis of 1: (a) Schultz, A. G.; Malachowski, W. P.; Pan, Y. J. Org. Chem. 1997, 62, 1223; (b) Desmaële, D.; Mekouar, K.; d'Angelo, J. J. Org. Chem. 1997, 62, 3890.
    • (1997) J. Org. Chem. , vol.62 , pp. 1223
    • Schultz, A.G.1    Malachowski, W.P.2    Pan, Y.3
  • 8
    • 0030754465 scopus 로고    scopus 로고
    • For the most recent enantioselective total synthesis of 1: (a) Schultz, A. G.; Malachowski, W. P.; Pan, Y. J. Org. Chem. 1997, 62, 1223; (b) Desmaële, D.; Mekouar, K.; d'Angelo, J. J. Org. Chem. 1997, 62, 3890.
    • (1997) J. Org. Chem. , vol.62 , pp. 3890
    • Desmaële, D.1    Mekouar, K.2    D'Angelo, J.3
  • 9
    • 0342516747 scopus 로고
    • Reviews or articles presenting comprehensive literature coverage on synthetic efforts directed to eburnane alkaloids: (a) Rahman, A.-U.; Sultana, M. Heterocycles 1984, 22, 841; (b) Ref. 8b; (c) Node, M.; Nagasawa, H.; Fuji, K. J. Org. Chem. 1990, 55, 517.
    • (1984) Heterocycles , vol.22 , pp. 841
    • Rahman, A.-U.1    Sultana, M.2
  • 10
    • 85038178185 scopus 로고    scopus 로고
    • Ref. 8b
    • Reviews or articles presenting comprehensive literature coverage on synthetic efforts directed to eburnane alkaloids: (a) Rahman, A.-U.; Sultana, M. Heterocycles 1984, 22, 841; (b) Ref. 8b; (c) Node, M.; Nagasawa, H.; Fuji, K. J. Org. Chem. 1990, 55, 517.
  • 11
    • 0025021186 scopus 로고
    • Reviews or articles presenting comprehensive literature coverage on synthetic efforts directed to eburnane alkaloids: (a) Rahman, A.-U.; Sultana, M. Heterocycles 1984, 22, 841; (b) Ref. 8b; (c) Node, M.; Nagasawa, H.; Fuji, K. J. Org. Chem. 1990, 55, 517.
    • (1990) J. Org. Chem. , vol.55 , pp. 517
    • Node, M.1    Nagasawa, H.2    Fuji, K.3
  • 14
    • 85038191637 scopus 로고    scopus 로고
    • Ref. 8b
    • (c) Ref. 8b;
  • 16
    • 0344714802 scopus 로고
    • The pioneering work of Prof. Kuehne introduced the use of imminium perchlorates as intermediates in eburnane alkaloids chemistry: Kuehne, M. E. J. Am. Chem. Soc. 1964, 86, 2949.
    • (1964) J. Am. Chem. Soc. , vol.86 , pp. 2949
    • Kuehne, M.E.1
  • 22
    • 85038190118 scopus 로고    scopus 로고
    • note
    • Prof. Schlessinger's group effected a similar transformation employing much harsher conditions: Ref. 12.
  • 23
    • 0018115056 scopus 로고
    • It is noteworthy that in this work the Zn/AcOH reduction of a similar pentacyclic intermediate produced only the cis diastereomer
    • Buzas, A.; Retourne, C.; Jacquet, J. P.; Lavielle, G. Tetrahedron 1978, 34, 3001. It is noteworthy that in this work the Zn/AcOH reduction of a similar pentacyclic intermediate produced only the cis diastereomer.
    • (1978) Tetrahedron , vol.34 , pp. 3001
    • Buzas, A.1    Retourne, C.2    Jacquet, J.P.3    Lavielle, G.4
  • 24
    • 85038192343 scopus 로고    scopus 로고
    • note
    • D: Ref. 10b.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.