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.) | Zendy

Francke Wittko | Zendy; Schröder Frank | Zendy; Kohnle Ulrich | Zendy; Simon Matthias | Zendy

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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.

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