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Attempts directed towards the total synthesis of feigrisolide B resulted in the synthesis of lactones 1 and 2. The synthesis of 1 and 2 was achieved from d-glucose and l-malic acid, respectively, with a Ti(IV) mediated diastereoselective aldol reaction as the key step. The structures of both 1 and 2 revealed that the structure proposed for feigrisolide B is incorrect.
A facile and mild protocol for the synthesis of substituted tetrahydrofurans, 2-deoxy C-aryl glycoside and C-aryl glycosides is described by use of 20 mol% FeCl3 or Yb(OTf)3 as acid catalysts. The benzylic carbocation generated undergoes intramolecular substitution by the oxygen nucleophile to result the tetrahydrofurans and C-aryl glycosides.
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