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Quadrane Sesquiterpenes: Natural Sources, Biology, and Syntheses

✍ Scribed by Marc Presset; Yoann Coquerel; Jean Rodriguez


Book ID
102829934
Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
511 KB
Volume
2010
Category
Article
ISSN
1434-193X

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✦ Synopsis


Abstract

Quadranes, discovered with the isolation of (–)‐quadrone in 1978, are biologically active naturally occurring sesquiterpenes featuring a distinctive set of bi‐ to tetracyclic ring systems. The available data for this family of natural products, including isolation data, biosynthetic considerations, a comprehensive compilation of the reported biological activities, and an exhaustive survey of the synthetic work in this area so far, are critically analyzed.


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Simple and preparatively efficacious lipase-catalysed kinetic resolution of endo, endo-cis-bicyclo[3.3.0]octane-2,6-diol rac-3 has provided ready access to bicyclo[3.3.0]octane-2,6-diones (-)-2 and (+)-2 of high enantiomeric purity. These C 2 -symmetric diones have been further elaborated to the ses