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

Angewandte Chemie 48(29), 5366-5368, DOI: 10.1002/anie.200902079

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.