Stereoselective Synthesis of the Antileukemic Sesquiterpene (+)-Caparratriene from L-menthol and Tiglic Aldehyde

Vydrina, V.A.; Kravchenko, A.A.; Yakovleva, M.P.; Ishmuratova, N.M.; Ishmuratov, G.Yu

Stereoselective Synthesis of the Antileukemic Sesquiterpene (+)-Caparratriene from L-menthol and Tiglic Aldehyde

2018

Vydrina, V.A. | Kravchenko, A.A. | Yakovleva, M.P. | Ishmuratova, N.M. | Ishmuratov, G.Yu

A stereoselective synthesis of natural (+)-caparratriene was developed starting from commercially available L-menthol and tiglic aldehyde. The key step was a Wittig reaction of the latter with the triphenylphosphorane generated from (R)-(–)-citronellyl bromide. (+)-Caparratriene as a mixture (4:1) of 2E,4E- and 2E,4Z-stereoisomers is a known anticancer agent.

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