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Pheromone synthesis CLXIX . Improved synthesis of the racemate of the hemiacetal pheromone of the spined citrus bug Biprorulus bibax
Author(s) -
Amaike Masayasu,
Mori Kenji
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199508197
Subject(s) - hemiacetal , pheromone , chemistry , stereochemistry , sex pheromone , botany , biology
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.