Novel Epothilone Lactones by an Unusual Diversion of the Grubbs' Metathesis Reaction

• Type of Material: Article
• Authors: Qiao-Hong Chen, Virginia Polytechnic Institute and State University; Thota Ganesh, Emory University; Yi Jiang, Emory University; Abhijit Banerjee, State University of New York of Binghamton; Shubhada Sharma, State University of New York of Binghamton; Susan Bane, Emory University; James P Snyder, Emory University; David G. I. Kingston, Virginia Polytechnic Institute and State University
• Language: English
• Date: 2010-03-28
• Publisher: Royal Society of Chemistry
• Publication Version: Author Accepted Manuscript (After Peer Review)
• Copyright Statement: © The Royal Society of Chemistry 2010
• Final Published Version (URL): http://pubs.rsc.org/en/Content/ArticleLanding/2010/CC/b926174e
• Title of Journal or Parent Work: Chemical Communications
• ISSN: 1359-7345
• Volume: 46
• Issue: 12
• Start Page: 2019
• End Page: 2021
• Grant/Funding Information: We are grateful for support of this work by NIH Grant CA-69571 and by NSF Grant CHE-0619382 for purchase of the Bruker Avance 600 spectrometer.
• Research Categories: Chemistry, General

Abstract

An unusual reaction with Grubbs’ catalyst during the synthesis of bridged epothilones yielded five-membered internal lactones instead of the expected metathesis products. Three of the lactones have comparable activities to epothilone D.