Abstract
Based upon the notion of a three carbon intercalation as a synthetic approach to texanes, a trans -perhydroindanone was required. In order to ensure the stereochemistry of the perhydroindanone, an approach based upon the stereocontrolled synthesis of a decalin followed by a ring contraction was adopted. In the course of this phase a C-acylation based upon the use of copper anolates was employed. A ring-contraction sequence was devloped initiated by a regioselective sulfenylation of a ketone. Acetoxylation of the resultant β-ketosulfide generated a monoprotected 1,2-diketone. Base treatment created a ring contracted α-hydroxycarboxylic acid which was cleaved directly to the nor-ketone. In this way, a suitable intermediate for elaboration into the taxanes was synthesized.
Published Version
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