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

Baumgartner, Corinne and Ma, Sandy and Liu, Qi and Stoltz, Brian M. (2010) Efforts toward rapid construction of the cortistatin A carbocyclic core via enyne-ene metathesis. Organic and Biomolecular Chemistry, 8 (13). pp. 2915-2917. ISSN 1477-0520. http://resolver.caltech.edu/CaltechAUTHORS:20100601-110245242

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1039/c004275gDOIArticle
http://pubs.rsc.org/en/Content/ArticleLanding/2010/OB/c004275gPublisherArticle
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
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.
Funders:
Funding AgencyGrant Number
King Abdullah University of Science and Technology (KAUST)KUS-11-006-02
AbbottUNSPECIFIED
AmgenUNSPECIFIED
Boehringer-IngelheimUNSPECIFIED
Bristol-Myers SquibbUNSPECIFIED
MerckUNSPECIFIED
Sigma-Aldrich UNSPECIFIED
CaltechUNSPECIFIED
NSFCHE-0639094
Record Number:CaltechAUTHORS:20100601-110245242
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20100601-110245242
Official Citation:Corinne Baumgartner, Org. Biomol. Chem., 2010, DOI: 10.1039/c004275g
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:18501
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:28 Jun 2010 16:18
Last Modified:15 Feb 2017 19:33

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