Asymmetric total synthesis of glycinoeclepin A: Generation of a novel bridgehead anion species

Abstract

The asymmetric total synthesis of glycinoeclepin A, a hatchstimulating agent of the soybean, cyst nematode, was accomplished on the basis of a cyclopentene annulation for constructing the CD ring moiety having contiguous quaternary carbon atoms. Introduction of the A ring moiety was achieved by an alkylation reaction using a 7-oxabicyclo[2.2.1]hex-l-yl anion species. © 2010 The Chemical Society of Japan.