For the assignment of the configuration at C(8) and C(15) of the natural oviposition-deterring pheromone 1 in Rhagoletis cerasi L., the four possible stereoisomers of 1 are synthesized. By condensing the C, building blocks (5R)-4 and (5S)-4 with the boron enolates of the C,, building blocks (4S)-13
Pheromone synthesis, CLX. A new synthesis of the oviposition-deterring pheromone of the European cherry fruit flyRhagoletis cerasi L.
✍ Scribed by Mori, Kenji ;Qian, Zhao-Hui
- Publisher
- John Wiley and Sons
- Year
- 1994
- Tongue
- English
- Weight
- 559 KB
- Volume
- 1994
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
Abstract
A new synthesis of the ammonium salt 1c of (8__RS__,15__R__)‐N‐[(β‐D‐glucopyranosyloxy)‐8‐hydroxypalmitoyl]taurine, the oviposition‐deterring pheromone of the European cherry fruit fly Rhagoletis cerasi L., was achieved by starting from 2,3,4,6‐tetra‐O‐pivaloyl‐α‐D‐glucopyranosyl bromide (2), taurine (4), ethyl (R)‐3‐hydroxybutanoate (5), propargyl alcohol (6), methyl acetoacetate (7), and 1,6‐hexanediol (8). magnified image
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