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Merck

Concise total synthesis of (-)-8-epigrosheimin.

Organic letters (2011-06-17)
Haishen Yang, Yuzhe Gao, Xiaoxiao Qiao, Longguan Xie, Xiaohua Xu
ABSTRACT

A highly efficient route was developed to synthesize (-)-8-epigrosheimin in four steps from aldehyde 2 based on a substrate-controlled method. The key steps of the synthesis included (1) a stereo- and regioselective allylation addition, (2) an intramolecular translactonization, and (3) an aldehyde-ene cyclization.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
L-Carvone, natural, 99%, FG
Sigma-Aldrich
L-Carvone, ≥97%, FCC, FG
Supelco
(+)-Carvone, certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland
Sigma-Aldrich
(S)-(+)-Carvone, 96%
Sigma-Aldrich
D-Carvone, ≥96%, FG
Sigma-Aldrich
(R)-(−)-Carvone, 98%
Supelco
(+)-Carvone, analytical standard
Supelco
(−)-Carvone, analytical standard