Stereoselective synthesis of (±)-β-elemene by a doubly diastereodifferentiating internal alkylation: a remarkable difference in the rate of enolization between syn and anti esters

초록

A total synthesis of the sesquiterpene (+/-)-p-elemene (1) has been achieved starting from a simple acyclic precursor 4. Key transformations include a 'doubly diastereodifferentiating folding and allylic strain-controlled' intramolecular ester enolate alkylation. In the course of the synthesis, we encountered remarkably different reactivity between syn and anti diastereomeric esters in the enolization step. (C) 2001 Elsevier Science Ltd. All rights reserved.

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