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Synthesis of sesquiterpene alcohols from calarene and thujopsene
Author(s) -
Bombarda Isabelle,
Gaydou Emile M.,
Faure Robert,
Smadja Jacqueline
Publication year - 1997
Publication title -
flavour and fragrance journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.393
H-Index - 70
eISSN - 1099-1026
pISSN - 0882-5734
DOI - 10.1002/(sici)1099-1026(199707)12:4<227::aid-ffj651>3.0.co;2-i
Subject(s) - chemistry , sesquiterpene , organic chemistry , selectivity , terpene , catalysis
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. © 1997 John Wiley & Sons, Ltd.