Synthesis and Cycloaromatization of a Neocarzinostatin Chromophore Analogue Equipped with an Intramolecular Nucleophile

All articles of this category A new 10 membered ring analogue of neocarzinostatin chromophore 4 [12-(2-acetylthioethyl)-7,7-dimethyl-5-oxobicyclo-[8.3.0]trideca-1(2),10(11)-diene-3,8-diyne] equipped with the acetylthioethane group undergoes intramolecular conjugate addition of the corresponding thiolate under weakly basic methanolysis conditions leading to reductive cycloaromatization to give the benz[5,6]indeno[1,2- b ]thiophene ring system. The intermediacy of the phenyl radical 19 has been supported by the abstraction of carbon-bound deuterium.