Enantioselective synthesis of the epoxy diyne core of neocarzinostatin chromophore

AG Myers, PM Harrington, EY Kuo

Index: Myers; Harrington; Kuo Journal of the American Chemical Society, 1991 , vol. 113, # 2 p. 694 - 695

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Citation Number: 109

Abstract

The chromophore component (1)'of the antitumor agent neocarzinostatin2 exhibits potent cytotoxicity and DNA-cleaving a~ tivity.~ DNA cleavage is believed to be initiated by an exceptionally facile nucleophilic addition of thiol to C12 of 1 followed by a rapid rearrangement reaction leading to the formation of a carbon-centered biradi~ al.~ The highly strained carbocyclic skeleton of 1 and unusual assembly of functional groups along its ...