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Pheromone synthesis CLXIX. Improved synthesis of the racemate of the hemiacetal pheromone of the spined citrus bugBiprorulus bibax

✍ Scribed by Amaike, Masayasu ;Mori, Kenji

Publisher
John Wiley and Sons
Year
1995
Tongue
English
Weight
360 KB
Volume
1995
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The racemate of (3__R__,4__S__,1′E)‐3,4‐bis(1′‐butenyl)tetrahydro‐2‐furanol (1) was synthesized by employing Ireland's ester enolate Claisen rearrangement of (±)‐5 as the key step. The synthesis was efficient enough to provide 23.7 g of (±)‐1 in 41% overall yield based on (±)‐7 (8 steps) without having recourse to such a toxic solvent as HMPA in the key step.

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