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

Author

Trenkle JD and Jamison TF

Subjects
Boranes chemistry, Catalysis, Cyclization, Oxidation-Reduction, Phosphines chemistry, Stereoisomerism, Alkynes chemistry, Epoxy Compounds chemistry, Lactones chemical synthesis, Nickel chemistry
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.

Published
2009
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