Synthesis of sesquiterpene alcohols from calarene and thujopsene

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 LiAlH4 and LiEt3BH 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. © 1997 John Wiley & Sons, Ltd.