TY - JOUR
T1 - Pheromone Synthesis, CLVII. Synthesis of the Enantiomers of syn‐4‐Methyl‐5‐nonanol to Determine the Absolute Configuration of the Naturally Occurring (4S,5S) Isomer Isolated as the Male‐produced Pheromone Compound of Rhynchophorus vulneratus and Metamasius hemipterus
AU - Mori, Kenji
AU - Kiyota, Hiromasa
AU - Malosse, Christian
AU - Rochat, Didier
PY - 1993
Y1 - 1993
N2 - The enantioselective synthesis of both (4R,5R)‐ and (4S,5S)‐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 (4S,5S)‐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.
AB - The enantioselective synthesis of both (4R,5R)‐ and (4S,5S)‐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 (4S,5S)‐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.
KW - Asian palm weevil
KW - Epoxides
KW - Metamasiums hemipterus
KW - Pheromones
KW - Rhynchophorus vulneratus
UR - http://www.scopus.com/inward/record.url?scp=84986644304&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84986644304&partnerID=8YFLogxK
U2 - 10.1002/jlac.1993199301194
DO - 10.1002/jlac.1993199301194
M3 - Article
AN - SCOPUS:84986644304
SN - 0075-4617
VL - 1993
SP - 1201
EP - 1204
JO - Justus Liebigs Annalen der Chemie
JF - Justus Liebigs Annalen der Chemie
IS - 11
ER -