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

Authors

Ahmad S. Altiti, CUNY Hunter College
David R. Mootoo, CUNY Hunter CollegeFollow

Document Type

Article

Publication Date

February 2015

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 work was originally published in Organic Letters, available at doi:10.1021/ol5002686.