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Determination of the absolute configuration at C-6 and C-7 of serricornin (4,6-dimethyl-7-hydroxy-3-nonanone), the sex pheromone of the cigarette beetle

✍ Scribed by Kenji Mori; Hiroko Nomi (née Iwasawa); Tatsuji Chuman; Masahiro Kohno; Kunio Kato; Masao Noguchi

Publisher: Elsevier Science
Year: 1981
Tongue: French
Weight: 228 KB
Volume: 22
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)90254-0

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✦ Synopsis

The absolute configuration at C-6 and C-7 of serricornin was established as (6S, 75) by synthesizing its (65, 7S)-erythro and (6R, 7R)threo isomers.

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A structure of the sex pheromone produced by the female cigarette beetle (Lasioderma serricorne F.) is established as 4,6-dimethyl-7-hydroxy-nonan-3-one (Ia) by chemical and spectroscopic evidences.

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## Sumnary: The absolute stereochemistry of serricornin was determined to be (4S,6S,7S) by the synthesis of its (4S,6R,7R)-isomer using a carbohydrate synthon. ## Serricornin (la)[ 4,6-dimethyl-7-hydroxynonan-3-one ] is the sex pheromone of the female -

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