PHEROMONE SYNTHESIS .154. SYNTHESIS OF THE STEREOISOMERS OF 3-METHYL-4-OCTANOL TO DETERMINE THE ABSOLUTE-CONFIGURATION OF THE NATURALLY-OCCURRING (3S,4S)-ISOMER ISOLATED AS THE MALE-PRODUCED AGGREGATION PHEROMONE OF THE AFRICAN PALM WEEVIL, RHYNCHOPHORUS-PHOENICIS

Authors
MORI K KIYOTA H ROCHAT D
Citation
K. Mori et al., PHEROMONE SYNTHESIS .154. SYNTHESIS OF THE STEREOISOMERS OF 3-METHYL-4-OCTANOL TO DETERMINE THE ABSOLUTE-CONFIGURATION OF THE NATURALLY-OCCURRING (3S,4S)-ISOMER ISOLATED AS THE MALE-PRODUCED AGGREGATION PHEROMONE OF THE AFRICAN PALM WEEVIL, RHYNCHOPHORUS-PHOENICIS, Liebigs Annalen der Chemie, (8), 1993, pp. 865-870
Citations number
11
Categorie Soggetti
Chemistry
Journal title
Liebigs Annalen der Chemie → ACNP
ISSN journal
01702041
Issue
8
Year of publication
1993
Pages
865 - 870
Database
ISI
SICI code
0170-2041(1993):8<865:PS.SOT>2.0.ZU;2-I
Abstract
The relative configuration of the naturally occurring 3-methyl-4-octan ol (1), the male-produced aggregation pheromone of Rhynchophorus phoen icis, was determined as syn by a GC comparison of the synthetic (+/-)- syn- and (+/-)-anti-1 with the natural product. Enantioselective synth esis of both (3R,4R)- and (3S,4S)-l was achieved by starting from the optically active epoxide 9, and the natural product was shown to be (3 S,4S)-l by a GC comparison on a chiral stationary phase.