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

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Abstract
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.

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