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Synthesis of (1S,2R,5R)-2-Ethyl-1,5-dimethyl-6,8-dioxabicyclo[3.2.1]octane, the Aggregation Pheromone of Male Beech Bark Beetles,Taphrorychus bicolor (Col., Scol.)

✍ Scribed by Francke, Wittko ;Schröder, Frank ;Kohnle, Ulrich ;Simon, Matthias

Publisher
John Wiley and Sons
Year
1996
Tongue
English
Weight
579 KB
Volume
1996
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The absolute configuration of the new bicyclic acetal 2‐ethyl‐1,5‐dimethyl‐6,8‐dioxabicyclo[3.2.1]octane (1), identified as an aggregation pheromone of males of the beech bark beetle, Taphrorychus bicolor, was determined by unambiguous synthesis and NMR experiments. The syntheses of the racemates of both diastereomers and of optically pure samples are described. The natural product proved to show (1__S__,2__R__,5__R__) configuration.

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