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Synthesis of a stereoisomeric mixture of 2,3-dihydro-2,3,5-trimethyl-6-(1-methyl-1-oxobutyl)-4H-pyran-4-one, the pheromone of the drugstore beetle

✍ Scribed by Masayuki Sakakibara; Kenji Mori

Publisher: Elsevier Science
Year: 1979
Tongue: French
Weight: 141 KB
Volume: 20
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)86303-6

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✦ Synopsis

Reaction of acetaldehyde with the trianion of 4,6-dimethylnonane-3,5, 7-trione followed by acidification yielded a stereoisomeric mixture of the pheromone of Stegobium paniceum L. The sex pheromone produced by the female drugstore beetle, Stegobium paniceum L., was recently isolated,' and the structure 4&was assigned to it on the basis of chemical and spectroscopic evidence. 2 Here we record a simple biomimetic synthesis of 2 as a mixture of two diastereomeric racemates. The synthetic scheme shown below is based on the recent progress in the chemistry of diand trianions.

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