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

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

doi:10.1039/c004275g

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

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

Research output: Contribution to journal › Article › peer-review

37 Scopus citations

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.

Original language	English (US)
Pages (from-to)	2915
Journal	Organic & Biomolecular Chemistry
Volume	8
Issue number	13
DOIs	https://doi.org/10.1039/c004275g
State	Published - 2010
Externally published	Yes

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledged KAUST grant number(s): KUS-11-006-02
Acknowledgements: 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.
This publication acknowledges KAUST support, but has no KAUST affiliated authors.

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title = "Efforts toward rapid construction of the cortistatin A carbocyclic core via enyne-ene metathesis",

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. {\textcopyright} 2010 The Royal Society of Chemistry.",

author = "Corinne Baumgartner and Sandy Ma and Qi Liu and Stoltz, {Brian M.}",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledged KAUST grant number(s): KUS-11-006-02 Acknowledgements: 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. This publication acknowledges KAUST support, but has no KAUST affiliated authors.",

year = "2010",

doi = "10.1039/c004275g",

language = "English (US)",

volume = "8",

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journal = "Organic & Biomolecular Chemistry",

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publisher = "Royal Society of Chemistry",

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T1 - Efforts toward rapid construction of the cortistatin A carbocyclic core via enyne-ene metathesis

AU - Baumgartner, Corinne

AU - Ma, Sandy

AU - Liu, Qi

AU - Stoltz, Brian M.

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledged KAUST grant number(s): KUS-11-006-02 Acknowledgements: 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. This publication acknowledges KAUST support, but has no KAUST affiliated authors.

PY - 2010

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AB - 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.

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JO - Organic & Biomolecular Chemistry

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IS - 13

ER -

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

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