Synthesis of (±)-Cedrol

Keywords

(±)-cedrol - (±)-cedrone - sesquiterpene alcohol - Stork–Danheiser transposition - Simmons–Smith cyclopropanation - Collins oxidation

Significance

Corey and Balanson reported a concise synthesis of (±)-cedrone, which can be readily converted into the sesquiterpene alcohol (±)-cedrol. It features a tricyclo[5.3.1.0^1,5]undecane core that was assembled via a stereospecific cyclization reaction. To investigate the stereospecificity of this annulation, Corey and Balanson separated the two diastereomers of ketone G on preparative gas chromatography. The individual diastereomers were subjected to cyclization conditions, furnishing either (±)-cedrone or (±)-epi-cedrone.

Comment

Enone D was prepared from enol ether B via Stork–Danheiser transposition. Reduction of the carbonyl group followed by Simmons–Smith cyclopropanation and subsequent oxidation of the alcohol furnished ketone G with a diastereomeric ratio of 1:1. The diastereomeric mixture was treated with acetyl methanesulfonate (H) to yield (±)-cedrone and (±)-epi-cedrone with a combined yield of 85 %.

Publication History

Article published online:
16 December 2025