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Synthesis of (1 S ,2 R ,5 R )‐2‐Ethyl‐1,5‐dimethyl‐6,8‐dioxabicyclo[3.2.1]octane, the Aggregation Pheromone of Male Beech Bark Beetles, Taphrorychus bicolor (Col., Scol.)
Author(s) -
Francke Wittko,
Schröder Frank,
Kohnle Ulrich,
Simon Matthias
Publication year - 1996
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.199619961005
Subject(s) - octane , chemistry , pheromone , diastereomer , beech , bicyclic molecule , acetal , stereochemistry , bark (sound) , organic chemistry , botany , physics , biology , acoustics
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.