Synthetic studies on thiostrepton family of peptide antibiotics: Synthesis of the tetrasubstituted dihydroquinoline portion of siomycin D1

Abstract

The tetrasubstituted dihydroquinoline portion of siomycin D1, a member of the thiostrepton family of peptide antibiotics, was synthesized from 5,6,7,8-tetrahydroquinoline featuring the modified Reissert-Henze reaction, the homolytic aromatic substitution reaction, the modified Boekelheide rearrangement, and the Jacobsen asymmetric epoxidation.