Asymmetric conjugate addition for the preparation of syn-1,3-dimethyl arrays: synthesis and structure elucidation of capensifuranone.

The synthesis of capensifuranone (1) has been achieved by the application of developments for asymmetric conjugate addition reactions of organocopper reagents with nonracemic N-enoyl-4-phenyl-1,3-oxazolidinones for the preparation of 1,3-syn-dimethyl arrays. The assignment of relative and absolute stereochemistry of 1 has been made following the high-field NMR characterizations of synthetic diol derivatives. The previously unassigned C4 stereochemistry of 1 was determined to be of the (S)-configuration. The thermodynamic equilibration of capensifuranone and its C4 diastereomer has been examined. Copyright 2004 American Chemical Society