Angewandte Chemie. International edition in English 2009-01-01

Macrocyclization by nickel-catalyzed, ester-promoted, epoxide-alkyne reductive coupling: total synthesis of (-)-gloeosporone.

James D Trenkle, Timothy F Jamison

Index: Angew. Chem. Int. Ed. Engl. 48(29) , 5366-8, (2009)

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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.