A Short Intramolecular Diels−Alder Route to Himbacine Derivatives

The intramolecular cycloaddition of 5 yields the unsaturated lactones 17a, 17b, and 17c as three major isomeric adducts. These were further reduced to the corresponding derivatives 21a, 21b, and 21c, which are intermediates for the synthesis of (+)‐himbacine and stereoisomers thereof. Precursor 5 wa...

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Bibliographic Details
Published in:	European journal of organic chemistry Vol. 2001; no. 15; pp. 2851 - 2860
Main Authors:	Hofman, Sven, Gao, Ling-Jie, Van Dingenen, Hilde, Hosten, Noël G. C., Van Haver, Dirk, De Clercq, Pierre J., Milanesio, Marco, Viterbo, Davide
Format:	Journal Article
Language:	English
Published:	Weinheim WILEY-VCH Verlag GmbH 01-08-2001 WILEY‐VCH Verlag GmbH
Subjects:	Cycloadditions Neurotransmitters Receptors Total synthesis
Online Access:	Get full text
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Summary:	The intramolecular cycloaddition of 5 yields the unsaturated lactones 17a, 17b, and 17c as three major isomeric adducts. These were further reduced to the corresponding derivatives 21a, 21b, and 21c, which are intermediates for the synthesis of (+)‐himbacine and stereoisomers thereof. Precursor 5 was obtained in a short convergent way using Sonogashira and Stille coupling reactions as the main C−C bond construction reactions.
Bibliography:	ark:/67375/WNG-SNHPZ7RD-1 istex:D036E536AE60402B9A27BD846DE4EB97A0E9213E ArticleID:EJOC2851
ISSN:	1434-193X 1099-0690
DOI:	10.1002/1099-0690(200108)2001:15<2851::AID-EJOC2851>3.0.CO;2-U