Total synthesis of quinocarcin and its related compounds

Abstract

This chapter presents the synthetic studies on quinocarcin and its related compounds including three independent total synthesis, focusing particularly on their strategies. The chapter discusses various synthetic methodologies devised for constructing the requisite ring systems and functional groups with correct stereochemistry. The synthetic method derived in the chapter, which provides both enantiomers of various structural types of quinocarcin congeners with definite absolute configurations that seems to be superior to those explored by other research groups in both efficiency and flexibility. The studies on structure-activity relationships presented in the chapter, might be useful for both elucidating the mode of action and developing more effective anticancer agents. The total synthesis of racemic quinocarcinol was achieved by Danishefsky et al. The key step in this approach is envisaged to be a Lewis acid-promoted double cyclization of the tetrahydroisoquinoline through the intermediate oxonium ion to construct the requisite tetracyclic ring system in a single operation.