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

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

Type

Article

Authors

Baumgartner, Corinne
Ma, Sandy
Liu, Qi
Stoltz, Brian M.

KAUST Grant Number

KUS-11-006-02

Date

2010

Permanent link to this record

http://hdl.handle.net/10754/598122

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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. © 2010 The Royal Society of Chemistry.

Citation

Baumgartner C, Ma S, Liu Q, Stoltz BM (2010) Efforts toward rapid construction of the cortistatin A carbocyclic core via enyne-ene metathesis. Org Biomol Chem 8: 2915. Available: http://dx.doi.org/10.1039/c004275g.

Sponsors

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.