Formal synthesis of the antitumour antibiotic CC-1065

Abstract

A formal total synthesis of the potent antitumour antibiotic CC-1065 (1) is described; both the cyclopropapyrroloindole (2) and the ‘dimeric’ pyrroloindole (3) are synthesized by routes involving vinyl azide chemistry. The cyclopropapyrroloindole (2) is prepared from 5-benzyloxy-2-bromoacetophenone (Schemes 3–5), the key steps being the formation of both indoles by decomposition of the azides (9) and (13). The dimer (3) is prepared by coupling the monomeric pyrroloindoles (25) and (27), followed by functional group transformations (Scheme 7).