Enantioselective synthesis of (+)-cortistatin a, a potent and selective inhibitor of endothelial cell proliferation

Hong Myung Lee; Cristina Nieto-Oberhuber; Matthew D Shair

doi:10.1021/ja8071918

Enantioselective synthesis of (+)-cortistatin a, a potent and selective inhibitor of endothelial cell proliferation

J Am Chem Soc. 2008 Dec 17;130(50):16864-6. doi: 10.1021/ja8071918.

Authors

Hong Myung Lee¹, Cristina Nieto-Oberhuber, Matthew D Shair

Affiliation

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

PMID: 19053422
DOI: 10.1021/ja8071918

Abstract

This manuscript describes an enantioselective synthesis of the naturally occurring inhibitor of endothelial cell proliferation, cortistatin A. Key steps of the synthesis are a silicate-directed elimination/ring expansion reaction and a highly diastereoselective aza-Prins cyclization with a subsequent transannular etherification.

Publication types

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

MeSH terms

Cell Proliferation / drug effects
Endothelial Cells / cytology*
Endothelial Cells / drug effects*
Molecular Structure
Neuropeptides / chemical synthesis*
Neuropeptides / chemistry
Neuropeptides / pharmacology*
Stereoisomerism

Substances

Neuropeptides
cortistatin