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Pheromone Synthesis, CXVII Synthesis of Sitophilate, the Aggregation Pheromone ofSitophilus granarius L., and Its Antipode

✍ Scribed by Mori, Kenji ;Ishikura, Masaharu

Publisher: John Wiley and Sons
Year: 1989
Tongue: English
Weight: 319 KB
Volume: 1989
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.1989198902101

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✦ Synopsis

The granary weevil (Sitophilus granarius L.) is a cosmopolitan pest of stored cereal grains. Its male-produced aggregation pheromone was isolated, named sitophilate, and identified by Phillips et al. as 1-ethylpropyl (2R*,3S*)-3-hydroxy-2-methylpentanoate2) (1). A synthesis of the enantiomers of 1 by employing Sharpless asym-Scheme I (4S,SR)-Sitophilure 3 R=H, R'-Me 4 R=TBS, R'=Me 5 R=TBS, R'=H

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