Three-step synthesis of cyclopropyl peptidomimetics

Norma Dunlap; Kevin R Lankford; Anuradha Liyana Pathiranage; Jessica Taylor; Nikhil Reddy; Daniel Gouger; Phillip Singer; Kent Griffin; Joseph Reibenspies

doi:10.1021/ol201828u

Three-step synthesis of cyclopropyl peptidomimetics

Org Lett. 2011 Sep 16;13(18):4879-81. doi: 10.1021/ol201828u. Epub 2011 Aug 24.

Authors

Norma Dunlap¹, Kevin R Lankford, Anuradha Liyana Pathiranage, Jessica Taylor, Nikhil Reddy, Daniel Gouger, Phillip Singer, Kent Griffin, Joseph Reibenspies

Affiliation

¹ Middle Tennessee State University, Department of Chemistry, Murfreesboro, Tennessee 37132, USA. ndunlap@mtsu.edu

PMID: 21863816
DOI: 10.1021/ol201828u

Abstract

An efficient approach to novel cyclopropyl peptidomimetics has been developed. The synthetic route involves a cyclopropanation using ethyl (dimethylsulfuranylidene)acetate (EDSA) as the key step and affords a cyclopropyl peptidomimetic core in three steps from protected amino acid Weinreb amides.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Crystallography, X-Ray
Cyclization
Cyclopropanes / chemical synthesis*
Cyclopropanes / chemistry
Models, Molecular
Molecular Structure
Peptidomimetics / chemical synthesis*
Peptidomimetics / chemistry
Stereoisomerism

Substances

Cyclopropanes
Peptidomimetics
cyclopropane