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

Stereoselective Synthesis of the Antileukemic Sesquiterpene (+)-Caparratriene from L-menthol and... 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. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Chemistry of Natural Compounds Springer Journals

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

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Publisher
Springer Journals
Copyright
Copyright © 2018 by Springer Science+Business Media, LLC, part of Springer Nature
Subject
Pharmacy; Pharmacy; Organic Chemistry; Plant Sciences
ISSN
0009-3130
eISSN
1573-8388
DOI
10.1007/s10600-018-2379-y
Publisher site
See Article on Publisher Site

Abstract

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.

Journal

Chemistry of Natural Compounds – Springer Journals

Published: Jun 6, 2018

References