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Enantioselective synthesis of cadinanes starting from R-(−)- or S-(+)-carvone

✍ Scribed by Alexander V. Baranovsky; Ben J.M. Jansen; Tommi M. Meulemans; Aede de Groot

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
659 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis

A new enantioselective synthesis of cadinanes, using the Mukaiyama-Michael reaction, was developed starting from R-(-)-or S-(+)-carvone. This approach gives an easy and direct access to the cadinane skeleton and the scope proved to be complementary to a formylation-annelation sequence. The applicability of the method was demonstrated by the enantioselective synthesis of 1,9--cadinadien-3-one and 4-methoxy-1,9-cadinadien-3-one.

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