Synthetic approaches to the total synthesis of plakortone B, as well as diastereoselective nucleophilic additions to furyl aldehyde and furyl sulfonylimine employing chiral 3-boronates as auxiliary are presented.

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An enantioselective synthesis of functionalized bicyclic lactones 2, 3 and 4, core structures of plakortones, are described; the configurations of 2, 3 and 4 were confirmed by X-ray crystallographic analyses of their precursors 11, 19 and 24, respectively.

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