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ChemInform Abstract

Mitsunobu reaction of the hydroxy acid (II) stereospecifically gives the lactone (III) with retention of the configuration at the origin of migration. This stereochemical course stands in contrast to Hudrlik′s observation that lactones with an embedded silylethyl carboxylate group sometimes undergo acid-catalyzed rearrangement with inversion of the configuration. Treatment of (III) with BF3×OEt3 causes mainly endocyclic elimination (→ (VII)) contradictory to Baldwin′s rule, suggesting that thus elimination follows an E1 pathway.