Silicon-mediated asymmetric synthesis of fagomine and 3,4-di- epi-fagomine

Abstract

The synthesis of d-fagomine and its stereoisomer, d-3,4-di- epi-fagomine has been achieved from C 2-symmetric 3,4-bis-silyl substituted adipic acid di-oxazolidin-2-one derivatives via stereocontrolled azidation and silicon to hydroxyl conversion as the key steps. The Evans oxazolidin-2-one controlled the stereochemical outcome of the azidation which supersedes the directing effects of the silyl substituent.