Total synthesis of the gilvocarcins

Abstract

This account describes our synthesis of the gilvocarcin-class aryl C-glycoside antibiotics. Particular attention has been given to the strategies and tactics developed during the study, which include (1) regio-and stereocontrolled aryl C-glycoside formation, and (2) regioselective [4 + 2] cycloaddition of 2-methoxyfuran with a sugar-bearing benzyne. A new method for the efficient generation of benzyne species at low temperature is also discussed. © 1995, The Society of Synthetic Organic Chemistry, Japan. All rights reserved.