Stereospecific Construction of Contiguous Quaternary and Tertiary Stereocenters by Rearrangement from Indoline‐2‐methanol to 2,2,3‐Trisubstituted Tetrahydroquinoline: Application to an Efficient Total Synthesis of Natural Virantmycin

Abstract

Only nine steps away: PPh3/CCl4-mediated stereospecific rearrangement of α,α-disubstituted indoline-2-methanol to 2,2,3-trisubstituted optically active tetrahydroquinoline (see scheme) has been developed. The reaction was applied to the first total synthesis of natural virantmycin, in only nine steps from commercially available starting material.