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Titolo:
Enantioselective syntheses of coronaridine and 18-methoxycoronaridine
Autore:
Kuehne, ME; Wilson, TE; Bandarage, UK; Dai, WN; Yu, Q;
Indirizzi:
Univ Vermont, Dept Chem, Burlington, VT 05405 USA Univ Vermont BurlingtonVT USA 05405 Dept Chem, Burlington, VT 05405 USA
Titolo Testata:
TETRAHEDRON
fascicolo: 11, volume: 57, anno: 2001,
pagine: 2085 - 2094
SICI:
0040-4020(20010310)57:11<2085:ESOCA1>2.0.ZU;2-G
Fonte:
ISI
Lingua:
ENG
Soggetto:
VINBLASTINE; IBOPHYLLIDINE; TABERSONINE;
Keywords:
enantioselective syntheses; coronaridine; 18-methoxycoronaridine;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
11
Recensione:
Indirizzi per estratti:
Indirizzo: Kuehne, ME Univ Vermont, Dept Chem, Burlington, VT 05405 USA Univ VermontBurlington VT USA 05405 Burlington, VT 05405 USA
Citazione:
M.E. Kuehne et al., "Enantioselective syntheses of coronaridine and 18-methoxycoronaridine", TETRAHEDRON, 57(11), 2001, pp. 2085-2094

Abstract

Condensation of indoloazepines bearing the chiral Nb-substituents: 1-(R)-naphthyl-alpha -ethyl, [1-(R)-[(S)-2-(diphenylphospheno)ferrocenyl]-ethyl], or 2,3-(R)-ferroceno-6,6-dimethyl-1-(S)-cyclohexyl, with 4-(1,3-dioxolan-2-yl)-hexanal, or with 4-(1,3-dioxolan-2-yl)-6-methoxyhexanal, gave diastereoselectively, through a secodine-type intramolecular Diels-Alder reaction, tetracyclic intermediates that could be carried to (-)-coronaridine or to the important anti-addictive (-)-18-methoxycoronaridine. The 2,3-(R)-ferroceno-6,6-dimethyl-1-O-cycrohexyl chiral auxiliary was most effective, providing >99% ee of a tetracyclic intermediate after removal of the chiral auxiliary group. (C) 2001 Elsevier Science Ltd. All rights reserved.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 10/07/20 alle ore 12:51:34