Versatile approaches for the synthesis of fused-ring γ-lactones utilizing cyclopropane intermediates

Timothy R Newhouse; Philip S J Kaib; Andrew W Gross; E J Corey

doi:10.1021/ol400362t

Versatile approaches for the synthesis of fused-ring γ-lactones utilizing cyclopropane intermediates

Org Lett. 2013 Apr 5;15(7):1591-3. doi: 10.1021/ol400362t. Epub 2013 Mar 7.

Authors

Timothy R Newhouse¹, Philip S J Kaib, Andrew W Gross, E J Corey

Affiliation

¹ Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, United States.

PMID: 23470216
DOI: 10.1021/ol400362t

Abstract

A highly effective acid-catalyzed cyclopropyl ester to γ-lactone skeletal rearrangement has been demonstrated and applied to the synthesis of a variety of bi- and tricyclic functionalized lactones, rigid and highly compact structures for use as biological probes.

Publication types

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

MeSH terms

Catalysis
Crystallography, X-Ray
Cyclopropanes / chemistry*
Esters
Lactones / chemical synthesis*
Lactones / chemistry
Molecular Conformation
Molecular Structure
Stereoisomerism

Substances

Cyclopropanes
Esters
Lactones
cyclopropane