✦ LIBER ✦
Pheromone Synthesis, CLVII. Synthesis of the Enantiomers ofsyn-4-Methyl-5-nonanol to Determine the Absolute Configuration of the Naturally Occurring (4S,5S) Isomer Isolated as the Male-produced Pheromone Compound ofRhynchophorus vulneratus andMetamasius hemipterus
✍ Scribed by Mori, Kenji ;Kiyota, Hiromasa ;Malosse, Christian ;Rochat, Didier
- Publisher
- John Wiley and Sons
- Year
- 1993
- Tongue
- English
- Weight
- 447 KB
- Volume
- 1993
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
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.