Tetrahedron Asymmetry p. 2923 - 2928 (1996)
Update date:2022-08-24
Topics:
Saito, Akiko
Tanaka, Akira
Oritani, Takayuki
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 allylic 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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