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.
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Williams et al. (2004) studied this question.
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