Abstract
In an effort to discover a versatile and convergent synthesis of pentacylic triterpenes, we have synthesized a tetracyclic enone via a highly stereocontrolled cycloaddition between a Nazarov precursor and a cyclohexenone followed by an aldol condensation. Introduction of a C14 nitrile was made by hydrocyanation on a protected derivative of this tetracyclic enone. Reduction and subsequent hydrolysis of the latter intermediate concluded this expedient synthesis of a pentacyclic lactone.
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