1'-hydroxy-tetrahydrofurans are found in many important biologically active natural products and are key structural features of the annonaceous acetogenins 1-3 (Scheme 1). The annonaceous acetogenins are known for possessing a range of interesting properties, including neurotoxicity, cytotoxicity, and pesticidal activity. There is a dearth of technology for the direct stereoselective and regioselective synthesis of 1'hydroxy-tetrahydrofurans. Radical additions into aldehydes, ring opening of epoxides, and nucleophilic additions into tetrahydrofuran carbaldehydes generally furnish mixtures of diastereomers or regioisomers. Our laboratory has a programmatic focus on the development of the di-tert-butyl silanol moiety into a synthetically useful auxiliary. During our exploration of epoxide opening reactions by pendant silanols, we serendipitously discovered an unprecedented rearrangement reaction of silanol epoxides into 1'-silanoxytetrahydrofurans. The uniqueness of this transformation prompted us to further explore its scope, mechanism, and potential applications. What follows is an account of our discoveries with this remarkable transformation.