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Volumn , Issue 18, 2007, Pages 2863-2867

Design for morphine alkaloids by intramolecular Heck strategy: Chemoenzymatic synthesis of 10-hydroxy-14-epi-dihydrocodeinone via C-D-B ring construction

Author keywords

Enzymatic dihydroxylation; Friedel Crafts reaction; Heck reaction; Mitsunobu reaction; Morphinans

Indexed keywords

10 HYDROXY 14 EPI DIHYDROCODEINONE; ALKADIENE; BETA BROMOETHYLBENZENE; ETHYLBENZENE; HYDROCODONE; MORPHINAN DERIVATIVE; MORPHINE; UNCLASSIFIED DRUG;

EID: 36549079966     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-990832     Document Type: Article
Times cited : (16)

References (45)
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    • For reviews of morphine syntheses, see: a
    • For reviews of morphine syntheses, see: (a) Zezula, J.; Hudlicky, T. Synlett 2005, 388.
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  • 5
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    • Hudlicky, T.; Butora, G.; Fearnley, S. P.; Gum, A. G.; Stabile, M. R. A Historical Perspective of Morphine Syntheses, In Studies in Natural Product Chemistry, 18; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1996, 43-154.
    • (e) Hudlicky, T.; Butora, G.; Fearnley, S. P.; Gum, A. G.; Stabile, M. R. A Historical Perspective of Morphine Syntheses, In Studies in Natural Product Chemistry, Vol. 18; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1996, 43-154.
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    • Organic Synthesis Highlights II; Waldmann, H., Ed.; VCH: Weinheim, 1995, 407.
    • (f) Organic Synthesis Highlights II; Waldmann, H., Ed.; VCH: Weinheim, 1995, 407.
  • 28
    • 0030733065 scopus 로고    scopus 로고
    • For synthesis of octahydroisoquinolines by electrochemical cyclizations, see
    • For synthesis of octahydroisoquinolines by electrochemical cyclizations, see: Endoma, M. A.; Butora, G.; Claeboe, C. D.; Hudlicky, T. Tetrahedron Lett. 1997, 38, 8833.
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    • For the conversion of 5 into 15, see: Zezula, J. PhD Thesis; University of Florida: USA, 2003.
    • For the conversion of 5 into 15, see: Zezula, J. PhD Thesis; University of Florida: USA, 2003.
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    • For the description of model studies see ref. 1a
    • For the description of model studies see ref. 1a.
  • 39
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    • Stereochemistry of C-10 hydroxyl: Rapoport, H.; Masamune, S. J. Am. Chem. Soc. 1955, 77, 4330.
    • (c) Stereochemistry of C-10 hydroxyl: Rapoport, H.; Masamune, S. J. Am. Chem. Soc. 1955, 77, 4330.
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    • It is likely that the hydrogenation of neopine-type compounds only proceeds to the natural configuration at C-14 in systems containing the full phenanthrene core, which is not the case with 14 or 15. The scarcity of material precluded us from performing the C-10-C-11 closure prior to hydrogenation
    • It is likely that the hydrogenation of neopine-type compounds only proceeds to the natural configuration at C-14 in systems containing the full phenanthrene core, which is not the case with 14 or 15. The scarcity of material precluded us from performing the C-10-C-11 closure prior to hydrogenation.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.