Oxidative cyclization of tertiary pentenol derivatives forming 2,5,5-trisubstituted THF rings and the total synthesis of cyclocapitelline

Authors

Geoffrey A. Phillips
Cory Palmer
Andrew C. Stevens
Mattew L. Piotrowski
Daryyl SR Dekruyf
Brian Pagenkopf, University of Western OntarioFollow

Document Type

Article

Publication Date

10-2015

Journal

Tetrahedron Letters

Volume

56

Issue

44

First Page

6052

Last Page

6055

URL with Digital Object Identifier

http://dx.doi.org/10.1016/j.tetlet.2015.09.064

Abstract

The synthesis of 2,5,5-trisubstituted tetrahydrofuran rings was accomplished via the Mukaiyama aerobic oxidative cyclization of tertiary 5-pentenols employing the Co(nmp)₂catalyst. A variety of THFs were formed in moderate to good yield and diastereoselectivity. The method developed herein was successfully applied to an enantioselective total synthesis of cyclocapitelline.