Dancing Silanols: Stereospecific Rearrangements of Silanol Epoxides into Silanoxy-Tetrahydrofurans and Silanoxy-Tetrahydropyrans.

ABSTRACT: We have developed highly stereospecific rearrangements of silanol epoxides into 1'-silanoxy-tetrahydrofurans and 1'-silanoxy-tetrahydropyrans. Upon treatment with Ph₃CBF₄ and NaHCO₃ in CH₂Cl₂, 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.

SUBMITTER: Joshi H 

PROVIDER: S-EPMC10688609 | biostudies-literature | 2023 May

REPOSITORIES: biostudies-literature