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

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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Summary: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.
National Institute of General Medical Sciences (U.S.) (GM-72566)
National Science Foundation (U.S.) (CHE-9809061)
National Science Foundation (U.S.) (DBI-9729592)
National Institutes of Health (U.S.) (1S10RR13866-01)

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