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Functionality Propagation by Alkylative Oxidation of Cross-Conjugated Cycloheptadienyl Sulfones


  • We thank Karl Wood and Arlene Rothwell for MS data and Daniel Lee for elemental analyses. E.T. wishes to thank Pfizer, Inc. for a fellowship.


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Getting the most out of sulfur. Enantiopure epoxyvinyl sulfone 1 is transformed to syn- and anti-dienyl sulfones 2 and 3, respectively, by means of a nucleophilic methylation/sulfenylation/directed elimination reaction sequence. Compound 2 has been converted into termini-differentiated seven-carbon polypropionate segments found in five biologically significant natural products.