Synthetic and Cycloaromatization Studies on a Calicheamicin Model: An Example of Internal Quenching of the 1,4-Diyl Intermediate

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Abstract
A precursor to the calicheamicin bicyclic core structure in which the enediyne bridge has been replaced by a 3-OMs-1,5-hexadiyne unit was synthesized with the purpose of investigating its ability to undergo cycloaromatization under basic conditions. Products arising from internal 1,5-hydrogen atom transfer were obtained which was confirmed by deuterium labelling experiments.

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