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Pheromone Synthesis, CLVII. Synthesis of the Enantiomers of syn ‐4‐Methyl‐5‐nonanol to Determine the Absolute Configuration of the Naturally Occurring (4 S ,5 S ) Isomer Isolated as the Male‐produced Pheromone Compound of Rhynchophorus vulneratus and Metamasius hemipterus
Author(s) -
Mori Kenji,
Kiyota Hiromasa,
Malosse Christian,
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.1993199301194
Subject(s) - enantiomer , chemistry , enantioselective synthesis , epoxide , absolute configuration , stereochemistry , pheromone , total synthesis , optically active , organic chemistry , botany , catalysis , biology
Abstract The enantioselective synthesis of both (4 R ,5 R )‐ and (4 S ,5 S )‐4‐methyl‐5‐nonanol ( 1 ) was achieved by starting from an optically active epoxide 5 . A GC comparison on a chiral stationary phase of the synthetic enantiomers of 1 with the naturally occurring 1 was executed, and (4 S ,5 S )‐ 1 was shown to be identical with the natural 1 isolated as the male‐produced pheromone compound of the weevils Rhynchophorus vulneratus and Metamasius hemipterus .