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Macrocyclization by Nickel‐Catalyzed,Ester‐Promoted,Epoxide–Alkyne Reductive Coupling: Total Synthesis of (−)‐Gloeosporone
Authors:James D Trenkle Dr  Timothy F Jamison Prof Dr
Institution:1. Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139 (USA), Fax: (+1)?617‐324‐0253 http://web.mit.edu/chemistry/jamison;2. Current address: Gilead Sciences, 333 Lakeside Dr., Foster City, CA 94404 (USA)
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.
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Keywords:C?C coupling  cyclization  nickel  reductive coupling  total synthesis
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