Title

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

Document Type

Article

Publication Date

7-18-2008

Abstract

(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. © 2008 American Chemical Society.

Publication Source (Journal or Book title)

Journal of Organic Chemistry

First Page

5592

Last Page

5594

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