Studies on γ-Lactams: Synthesis of some 3-Aryl-1,3a,4,9b-tetrahydrobenzo[e]indole-2,5-dione Derivatives and its Implication in the Total Synthesis of Functionalized 17-Azasteroids

Abstract

The γ-lactam esters 3 and 10, prepared from anilinomalonates and 3-arylacryloyl chloride, are hydrolysed and selectively decarboxylated to the trans-acids 4 and 11; further homologation and cyclization produce the tri- and tetra-cyclic γ-lactam derivatives 8 and 15 that simulate the B-C-D/A-B-C-D ring system of many azasteroids.