Photochemical Bergman Cyclization and Related Photoreactions of Enediynes

Authored by: Igor V. Alabugin , Wang-Yong Yang , Runa Pal

CRC Handbook of Organic Photochemistry and Photobiology

Print publication date:  March  2012
Online publication date:  March  2012

Print ISBN: 9781439899335
eBook ISBN: 9781466561250
Adobe ISBN:

10.1201/b12252-24

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Abstract

Naturally occurring enediyne antibiotics 1 are often hailed as the most potent family of anticancer agents discovered to date. 2 These molecules were developed by microorganisms as the most powerful chemical warfare targeting cellular DNA with astounding efficiency. The key step in the chemical mechanism responsible for this activity is the transformation of the enediyne moiety to a reactive p-didehydrobenzene diradical (p-benzyne). This step, the simplest version of which is given in Scheme 23.1, is a cycloaromatization reaction called the Bergman cyclization. 3 The simultaneous formation of two radical centers is important because it results in the abstraction of two hydrogen atoms (one from each strand of a double-stranded (ds) DNA), which, after a sequence of reactions, ultimately leads to ds DNA cleavage. 4

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