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Enantioselective total syntheses of the novel tricyclic sesquiterpene hydrocarbons (+)- and (−)-kelsoene. Absolute configuration of the natural product

✍ Scribed by Goverdhan Mehta; K Srinivas

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
75 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

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 sesquiterpene hydrocarbon (+)-kelsoene 1 and ent-kelsoene (-)-1, respectively, thereby establishing the absolute configuration of the natural product. In the light of these results, the absolute configuration assigned earlier to (+)-kelsoene needs to be revised as (+)-1.

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