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Synlett 1993; 1993(1): 20-22
DOI: 10.1055/s-1993-22331
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Synthetic and Cycloaromatization Studies on a Calicheamicin Model: An Example of Internal Quenching of the 1,4-Diyl Intermediate

Hélène Audrain* , Troels Skrydstrup, Gerardo Ulibarri, David S. Grierson
  • *Institut de Chimie des Substances Naturelles, CNRS, F-91198 Gif-sur-Yvette, France
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Publication History

Publication Date:
19 March 2002 (online)

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A precursor to the calicheamicin bicyclic core structure in which the enediyne bridge has been replaced by a 3-OMs-1,5-hexadiyne unit was synthesized with the purpose of investigating its ability to undergo cycloaromatization under basic conditions.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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