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Synthesis of sesquiterpene alcohols from calarene and thujopsene

✍ Scribed by Isabelle Bombarda; Emile M. Gaydou; Robert Faure; Jacqueline Smadja

Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
175 KB
Volume
12
Category
Article
ISSN
0882-5734

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✦ Synopsis

Oxidation and reduction reactions on two sesquiterpene hydrocarbons, calarene 1 and thujopsene 7, have been investigated in order to produce inexpensive fragrances for perfumery. Oxidation using m-chloroperbenzoic acid gave epoxides, ketones and unsaturated alcohols with a fair selectivity. Reduction reactions with LiAlH 4 and LiEt 3 BH of the epoxidized and ketonic compounds gave sesquiterpenic alcohols in good yields. The structures of these compounds have been determined from concerted application of two-dimensional NMR techniques. Odour analysis of these derivatives should permit the selection of novel fragrance materials for perfumers.

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