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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 (3S,4S)-Isomer Isolated as the Male-produced Aggregation Pheromone of the African Palm Weevil,Rhynchophorus phoenicis

✍ Scribed by Mori, Kenji ;Kiyota, Hiromasa ;Rochat, Didier

Publisher: John Wiley and Sons
Year: 1993
Tongue: English
Weight: 650 KB
Volume: 1993
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.1993199301137

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✦ Synopsis

Abstract

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.

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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

✍ Mori, Kenji ;Kiyota, Hiromasa ;Malosse, Christian ;Rochat, Didier 📂 Article 📅 1993 🏛 John Wiley and Sons 🌐 English ⚖ 447 KB

## 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