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Volumn 38, Issue 51, 1997, Pages 8833-8836

Chemoenzymatic and electrochemical oxidations in the synthesis of octahydroisoquindines for conversion to morphine. Relative merits of radical vs. acid-catalyzed cyclizations

Author keywords

[No Author keywords available]

Indexed keywords

ISOQUINOLINE DERIVATIVE; MORPHINE;

EID: 0030733065     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10384-7     Document Type: Article
Times cited : (22)

References (24)
  • 10
    • 0000504788 scopus 로고
    • Waldmann, H., Ed.; VCH: Weinheim
    • (b) Maier, M. In Organic Synthesis Highlights II; Waldmann, H., Ed.; VCH: Weinheim, 1995; pp 357-369;
    • (1995) Organic Synthesis Highlights II , pp. 357-369
    • Maier, M.1
  • 12
    • 0029565069 scopus 로고
    • Stabile, M.R.; Hudlicky, T.; Meisels, M.L.; Butora, G.; Gum, A. G.; Fearnley, S. P.; Thorpe, A. J.; Ellis, M. R. Chirality 1995, 7, 556. The low yield in the alkylation step is caused by competing elimination to a styrene derivative. A potential for recycling of this material by a hydroboration/oxidation/displacement sequence exists as has been demonstrated for die conversion of 6 to 5 in the aforementioned reference.
    • (1995) Chirality , vol.7 , pp. 556
    • Stabile, M.R.1    Hudlicky, T.2    Meisels, M.L.3    Butora, G.4    Gum, A.G.5    Fearnley, S.P.6    Thorpe, A.J.7    Ellis, M.R.8
  • 16
    • 0001673091 scopus 로고
    • Trost, B. M.; Fleming, I., Eds.
    • For recent reviews of acyl-iminium ion cyclization see: (a) Hiemstra, H.; Speckamp, W. N. in Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I., Eds., 1991, 2, 1047;
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 1047
    • Hiemstra, H.1    Speckamp, W.N.2
  • 18
    • 0343621673 scopus 로고    scopus 로고
    • note
    • The relative stereochemistry of intermediates 15 was not determined. In the case of successful cyclization of the succinimide derivatives 13 the crude mixtures were converted to 3.
  • 19
    • 84925839548 scopus 로고    scopus 로고
    • University of Florida
    • Full x-ray crystallography data will be published in Acta Cryst. by Khalil Abboud, University of Florida.
    • Acta Cryst
    • Abboud, K.1
  • 20
    • 0342316675 scopus 로고    scopus 로고
    • All analytical and spectral data obtained were consistent with the structural assignments
    • All analytical and spectral data obtained were consistent with the structural assignments.
  • 22
    • 0001454765 scopus 로고
    • For examples of electrooxidation of substituted amides at the N-methylene position see: (a) Nyberg, K.; Servin, R. Acta Chem. Scand. 1976, 30, 640;
    • (1976) Acta Chem. Scand. , vol.30 , pp. 640
    • Nyberg, K.1    Servin, R.2
  • 23
    • 0000435096 scopus 로고
    • review
    • (b) Shono, T. Tetrahedron 1984, 40, 811 (review).
    • (1984) Tetrahedron , vol.40 , pp. 811
    • Shono, T.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.