Efforts toward rapid construction of the cortistatin A carbocyclic core via enyne-ene metathesis

Creators: Baumgartner, Corinne; Ma, Sandy; Liu, Qi; Stoltz, Brian M.

Abstract

Our efforts toward the construction of the carbocylic core of cortistatin A via an enyne-ene metathesis are disclosed. Interestingly, an attempted S_N2 inversion of a secondary mesylate in our five-membered D-ring piece gave a product with retention of stereochemistry.

Additional Information

© The Royal Society of Chemistry 2010. Received 17th March 2010, Accepted 4th May 2010. First published on the web 24th May 2010. C. B. thanks the Schweizerischer Nationalfonds (SNF) for a fellowship. This publication is based on work supported by Award No. KUS-11-006-02, made by King Abdullah University of Science and Technology (KAUST). Additionally, the authors thank Abbott, Amgen, Boehringer-Ingelheim, Bristol-Myers Squibb, Merck, Sigma-Aldrich and Caltech for generous funding. Mr Lawrence Henling and Dr Michael Day are gratefully acknowledged for X-ray crystallographic structural determination. The Bruker KAPPA APEXII X-ray diffractometer was purchased via an NSF CRIF:MU award to the California Institute of Technology, CHE-0639094. Dr David VanderVelde and Dr Scott Ross are acknowledged for NMR assistance. Dr Scott Virgil is acknowledged for helpful discussions.

Attached Files

Published - Baumgartner2010p10577Org_Biomol_Chem.pdf

Supplemental Material - c004275g.pdf

Files

Baumgartner2010p10577Org_Biomol_Chem.pdf

Files (5.0 MB)

Name	Size	Download all
Baumgartner2010p10577Org_Biomol_Chem.pdf md5:d015194364471eb34013b7735794c570	332.7 kB	Preview Download
c004275g.pdf md5:23af99c4a5b05ba75ec81f2d881ecb73	4.7 MB	Preview Download

Additional details

	All versions	This version
Views	0	0
Downloads	0	0
Data volume	0 Bytes	0 Bytes