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“One-Pot” Reductive Lactone Alkylation Provides a Concise Asymmetric Synthesis of Chiral Isoprenoid Targets

Author:
Cao, Jia, Perlmutter, Patrick
Source:
Organic letters 2013 v.15 no.17 pp. 4327-4329
ISSN:
1523-7052
Subject:
Lewis bases, alkylation, chemical structure, cotton, isoprenoids, lactones, odors, sex pheromones, vitamin E
Abstract:
An efficient method, based on nucleophilic addition to lactones followed by modified in situ Clemmensen reduction, provides a short synthetic route to chiral isoprenoid targets. The efficacy of this method has been exemplified through the synthesis of several targets including the commercial fragrance Rosaphen, the side chain of Zaragozic acid C, the cotton leaf sex pheromone, and the side chains of vitamin E.
Agid:
5785830