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Pheromone Synthesis, CXLIII. Synthesis and Absolute Configuration of the Hemiacetal Pheromone of the Spined Citrus Bug Biprorulus bibax
Author(s) -
Mori Kenji,
Amaike Masayasu,
Oliver James E.
Publication year - 1992
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1992199201194
Subject(s) - hemiacetal , pheromone , absolute configuration , chemistry , total synthesis , stereochemistry , sex pheromone , botany , biology
(3 S ,4 R ,1′ E )‐3,4‐Bis(1′‐butenyl) tetrahydro‐2‐furanol ( 1 ) was synthesized from 1,3‐butadiene and maleic anhydride by employing the HLADH‐catalyzed enzymatic oxidation of meso ‐diol 2 as the key step, and shown to be identical with the pheromone produced by the dorsal abdominal glands of the male spined citrus bug ( Biprorulus bibax ).
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