Abstract
Condensations between the tricyclic ketones 9, 19 and 23 and the sodio-lithio dianion of methyl acetoacetate lead to the conformationally restricted Mevinic acid relatives 12b, 20b and 26 respectively, following lactonization and selective reduction. The approach of the nucleophile is stereospecific in the first two instances but not in the last; explanations for this behaviour are given. The target compounds showed negligible HMGCoA reductase antagonism.
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