Enantioselective synthesis of (+)-cephalostatin 1

Kevin C Fortner; Darryl Kato; Yoshiki Tanaka; Matthew D Shair

doi:10.1021/ja906996c

Enantioselective synthesis of (+)-cephalostatin 1

J Am Chem Soc. 2010 Jan 13;132(1):275-80. doi: 10.1021/ja906996c.

Authors

Kevin C Fortner¹, Darryl Kato, Yoshiki Tanaka, Matthew D Shair

Affiliation

¹ Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.

PMID: 19968285
DOI: 10.1021/ja906996c

Abstract

This Article describes an enantioselective synthesis of cephalostatin 1. Key steps of this synthesis are a unique methyl group selective allylic oxidation, directed C-H hydroxylation of a sterol at C12, Au(I)-catalyzed 5-endo-dig cyclization, and a kinetic spiroketalization.

Publication types

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

MeSH terms

Antineoplastic Agents / chemical synthesis
Antineoplastic Agents / chemistry
Phenazines / chemical synthesis*
Phenazines / chemistry*
Spiro Compounds / chemical synthesis*
Spiro Compounds / chemistry*
Stereoisomerism
Steroids / chemical synthesis*
Steroids / chemistry*
Substrate Specificity

Substances

Antineoplastic Agents
Phenazines
Spiro Compounds
Steroids
cephalostatin I