Intramolecular Nitrogen Delivery for the Synthesis of C-Glycosphingolipids. Application to the C-Glycoside of the Immunostimulant KRN7000

Authors

Ahmad Sabri Altiti, CUNY Hunter CollegeFollow
David R. Mootoo, CUNY Hunter CollegeFollow

Document Type

Article

Publication Date

Winter 2-21-2014

Abstract

The key reaction in this approach to C-glycosphingolipids is the stereoselective iodocyclization of a sugar-linked homoallylic carbonimidothioate. E and Z reaction substrates were assembled in a convergent fashion via an alkene metathesis strategy and exhibited the same alkene facial selectivity in the iodocyclization irrespective of alkene geometry, although the E alkene was found to be less reactive.

Comments

This article was originally published in Organic Letters, available at dx.doi.org/10.1021/ol5002686. This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes.