Macrocyclization by Nickel-Catalyzed, Ester-Promoted, Epoxide-Alkyne Reductive Coupling: Total Synthesis of (−)-Gloeosporone
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Jamison_Macrocyclization by nickel.pdf
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Author(s)
Trenkle, James D.
Jamison, Timothy F.
Date Issued
June 2009
Journal
Angewandte Chemie International Edition
Publisher
Wiley Blackwell
Citation
Trenkle, James D., and Timothy F. Jamison. “Macrocyclization by Nickel-Catalyzed, Ester-Promoted, Epoxide-Alkyne Reductive Coupling: Total Synthesis of (−)-Gloeosporone.” Angewandte Chemie International Edition 48, no. 29 (July 6, 2009): 5366-5368.
Version
Author's final manuscript
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 C--C bond formation (see scheme; cod=cyclooctadiene). The synthesis was accomplished in 10 steps and in approximately 9 % overall yield.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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Creative Commons Attribution-Noncommercial-Share Alike 3.0
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DOI of Published Version
https://doi.org/10.1002/anie.200902079
