Asymmetric Total Synthesis of Glycinoeclepin A: Generation of a Novel Bridgehead Anion Species

Abstract

Abstract The asymmetric total synthesis of glycinoeclepin A, a hatch-stimulating 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-1-yl anion species.