Abstract
A possible enantiocontrolled route to cerorubenic acid-III (1) is described herein. The central elements of the approach take advantage of the ready availability of both optical antipodes of citronellol and of the tricyclic ketone 8. Although the absolute configuration of 1 is not kown, its relative stereochemistry has been established by X-ray crystallography. On this basis, it is possible to match the reaction partners with the long-range view of establishing experimentally the actual configuration of 1. Assembly of the two structural halves was accomplished via a vinylstannane intermediate whose construction required utilization of an intramolecular S N 2 displacement in order to overcome the weakly nucleophilic nature of a stannyl-substituted ester enolate
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