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Enantioselective Total Syntheses of Pallambins A-D.

The first enantioselective total syntheses of pallambins A-D have been achieved in 15 or 16 steps from known chiral cyclohexenone. Salient features of the work include a Pd-catalyzed oxidative cyclization to assemble the [3.2.1]-bicyclic moiety, an Eschenmoser-Claisen rearrangement/lactone formation sequence to construct the C ring, an intramolecular Wittig reaction to form the D ring. The described synthesis avoids protecting-group manipulations by designing highly chemo- and stereoselective transformations. During the course of this work, a Pd-catalyzed method for dehydrobromination of alfa-bromoketones was developed.