We have developed highly stereospecific rearrangements of silanol epoxides into 1'-silanoxy-tetrahydrofurans and 1'-silanoxy-tetrahydropyrans. Upon treatment with Ph 3 CBF 4 and NaHCO 3 in CH 2 Cl 2 , di-substituted trans -epoxide silanols rearrange into products with an erythro configuration; di-substituted cis -epoxide silanols give products with a threo configuration. We have used these reactions as key steps in the syntheses of (±)-solerone and (±)-muricatacin.