Macrocyclization by Nickel-Catalyzed, Ester-Promoted, Epoxide-Alkyne Reductive Coupling: Total Synthesis of (−)-Gloeosporone

Ringing the changes: The total synthesis of the title compound centers around a novel strategy that employs a nickel(0)-phosphine complex and triethyl borane in an efficient closure of a 14-membered ring through C--C bond formation (see scheme; cod=cyclooctadiene). The synthesis was accomplished in...

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Bibliographic Details
Main Authors: Trenkle, James D (Contributor), Jamison, Timothy F. (Contributor)
Other Authors: Massachusetts Institute of Technology. Department of Chemistry (Contributor)
Format: Article
Language:English
Published: Wiley Blackwell, 2013-11-13T14:21:44Z.
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Online Access:Get fulltext
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100 1 0 |a Trenkle, James D.  |e author 
100 1 0 |a Massachusetts Institute of Technology. Department of Chemistry  |e contributor 
100 1 0 |a Trenkle, James D.  |e contributor 
100 1 0 |a Jamison, Timothy F.  |e contributor 
700 1 0 |a Jamison, Timothy F.  |e author 
245 0 0 |a Macrocyclization by Nickel-Catalyzed, Ester-Promoted, Epoxide-Alkyne Reductive Coupling: Total Synthesis of (−)-Gloeosporone 
260 |b Wiley Blackwell,   |c 2013-11-13T14:21:44Z. 
856 |z Get fulltext  |u http://hdl.handle.net/1721.1/82095 
520 |a Ringing the changes: The total synthesis of the title compound centers around a novel strategy that employs a nickel(0)-phosphine complex and triethyl borane in an efficient closure of a 14-membered ring through C--C bond formation (see scheme; cod=cyclooctadiene). The synthesis was accomplished in 10 steps and in approximately 9 % overall yield. 
520 |a National Institute of General Medical Sciences (U.S.) (GM-72566) 
520 |a National Science Foundation (U.S.) (CHE-9809061) 
520 |a National Science Foundation (U.S.) (DBI-9729592) 
520 |a National Institutes of Health (U.S.) (1S10RR13866-01) 
546 |a en_US 
655 7 |a Article 
773 |t Angewandte Chemie International Edition