Support for this work was provided by the National Institute of General Medical Sciences (GM-72566). We are grateful to Li Li for obtaining mass spectrometric data for all compounds (MIT Department of Chemistry Instrumentation Facility, which is supported in part by the NSF (CHE-9809061 and DBI-9729592) and the NIH (1S10RR13886-01)).
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Communication
Macrocyclization by Nickel-Catalyzed, Ester-Promoted, Epoxide–Alkyne Reductive Coupling: Total Synthesis of (−)-Gloeosporone†
Article first published online: 17 JUN 2009
DOI: 10.1002/anie.200902079
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Trenkle, James D. and Jamison, Timothy F. (2009), Macrocyclization by Nickel-Catalyzed, Ester-Promoted, Epoxide–Alkyne Reductive Coupling: Total Synthesis of (−)-Gloeosporone. Angew. Chem. Int. Ed., 48: 5366–5368. doi: 10.1002/anie.200902079
- †
Publication History
- Issue published online: 1 JUL 2009
- Article first published online: 17 JUN 2009
- Manuscript Received: 17 APR 2009
Funded by
- National Institute of General Medical Sciences. Grant Number: GM-72566
- NSF. Grant Numbers: CHE-9809061, DBI-9729592
- NIH. Grant Number: 1S10RR13886-01
Keywords:
- C
![[BOND]](http://onlinelibrarystatic.wiley.com/undisplayable_characters/00f8ff.gif)
C coupling; - cyclization;
- nickel;
- reductive coupling;
- total synthesis
Abstract
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 CC bond formation (see scheme; cod=cyclooctadiene). The synthesis was accomplished in 10 steps and in approximately 9 % overall yield.