A short intramolecular Diels-Alder route to himbacine derivatives

Authors
Hofman, S Gao, LJ Van Dingenen, H Hosten, NGC Van Haver, D De Clercq, PJ Milanesio, M Viterbo, D
Citation
S. Hofman et al., A short intramolecular Diels-Alder route to himbacine derivatives, EUR J ORG C, (15), 2001, pp. 2851-2860
Citations number
42
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
15
Year of publication
2001
Pages
2851 - 2860
Database
ISI
SICI code
1434-193X(200108):15<2851:ASIDRT>2.0.ZU;2-B
Abstract
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 f or the synthesis of (+)-himbacine and stereoisomers thereof. Precursor 5 wa s obtained in a short convergent way using Sonogashira and Stille coupling reactions as the main C-C bond construction reactions.