Electrophile-induced ether transfer: Stereoselective synthesis of 2,6-disubstituted-3,4-dihydropyrans

Article abstract of DOI:10.1021/jo800704d

(Chemical Equation Presented) Stereoselective synthesis of trans-2,6-disubstituted-3,4-dihydropyrans has been achieved from a simple homoallylic alkoxyether via a three-step sequence: electrophile-induced ether transfer, cyclization, and functionalization, which is highlighted by a rare example of Ferrier rearrangement of allylic ether. This methodology was successfully implemented for the asymmetric synthesis of a C7-C17 fragment of swinholide A.