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Pheromone Synthesis, CLIV. Synthesis of the Stereoisomers of 3‐Methyl‐4‐octanol to Determine the Absolute Configuration of the Naturally Occurring (3 S ,4 S )‐Isomer Isolated as the Male‐produced Aggregation Pheromone of the African Palm Weevil, Rhynchophorus phoenicis
Author(s) -
Mori Kenji,
Kiyota Hiromasa,
Rochat Didier
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1993199301137
Subject(s) - chemistry , absolute configuration , enantioselective synthesis , natural product , stereochemistry , total synthesis , epoxide , pheromone , organic chemistry , botany , catalysis , biology
The relative configuration of the naturally occurring 3‐methyl‐4‐octanol ( 1 ), the male‐produced aggregation pheromone of Rhynchophorus phoenicis , was determined as syn by a GC comparison of the synthetic (±)‐ syn ‐ and (±)‐ anti ‐ 1 with the natural product. Enantioselective synthesis of both (3 R ,4 R )‐and (3 S ,4 S )‐ 1 was achieved by starting from the optically active epoxide 9 , and the natural product was shown to be (3 S ,4 S )‐ 1 by a GC comparison on a chiral stationary phase.