Annelation of 2,3-dimethylcyclohexanone. Synthetic proof for the stereochemistry of the sesquiterpene aristolone
- 1 December 1969
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 47 (23) , 4307-4312
- https://doi.org/10.1139/v69-714
Abstract
An efficient annelation of 2,3-dimethylcyclohexanone is described. The key step of this process involves the reaction of the enol lactone 16 with methyllithium, under carefully controlled conditions. The completely stereoselective conversion of the sesquiterpene (−)-aristolone (1) into the levorotatory decalone 22b is described. Comparison of the latter with the unambiguously synthesized racemic decalone 22a conclusively establishes the relative stereochemistry of aristolone (1).Keywords
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