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A Short Intramolecular Diels−Alder Route to Himbacine Derivatives
Author(s) -
Hofman Sven,
Gao LingJie,
Van Dingenen Hilde,
Hosten Noël G. C.,
Van Haver Dirk,
De Clercq Pierre J.,
Milanesio Marco,
Viterbo Davide
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200108)2001:15<2851::aid-ejoc2851>3.0.co;2-u
Subject(s) - intramolecular force , chemistry , cycloaddition , stille reaction , sonogashira coupling , stereochemistry , adduct , divergent synthesis , diels–alder reaction , medicinal chemistry , organic chemistry , palladium , catalysis
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.