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A practical synthesis of enantiomerically pure (−)-geosmin via highly diastereoselective reduction of (4aS,8S)-4,4a,5,6,7,8-hexahydro-4a,8-dimethyl-2(3H)-naphthalenone

✍ Scribed by Akiko Saito; Akira Tanaka; Takayuki Oritani

Publisher: Elsevier Science
Year: 1996
Tongue: English
Weight: 274 KB
Volume: 7
Category: Article
ISSN: 0957-4166
DOI: 10.1016/0957-4166(96)00383-7

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✦ Synopsis

An asymmetric synthesis of (-)-geosmin 1 via highly diastereoselective reduction of the enantiomerically pure title ketone 3 is described. Diisobutylaluminum hydride reduction of 3 in a mixed solvent of tetrahydrofuran and 1,2-dimethoxyethane led to aUylic alcohol 4 in 96% d.e., which by recrystallization from hexane, afforded a diastereomerically pure sample. This was then converted to 1 in high overall yield through a five-step reaction sequence including a completely stereoselective epoxidation of silyl ether 6 and a one-pot process of epoxy silyl ether 7 to mesylate 9.

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