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Merck

Total synthesis of (+)-cyperolone.

Organic letters (2012-02-14)
Philipp Klahn, Alexander Duschek, Clémence Liébert, Stefan F Kirsch
ABSTRACT

The total synthesis of (+)-cyperolone, an eudesmane-derived sesquiterpenoid from Cyperus rotundus, is described. The de novo synthesis was accomplished via a 15 step sequence starting from (R)-(-)-carvone. The synthetic route features a platinum-catalyzed cycloisomerization to rapidly construct the bicyclic core from a 3-silyloxy-1,5-enyne intermediate.

MATERIALS
Product Number
Brand
Product Description

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