Abstract
Abstract Some of our studies in the area of the enediyne antibiotics are discussed, with particular emphasis on the involvement of sulfur in these compounds. First, a model study for the ABC-ring system of the calicheamicin η11-oligosaccharide involving a [3,3]-sigmatropic rearrangement is described which enabled the stereoselective installation of the 4-thiosubstituenton the B-ring and which served as the cornerstone for the first synthesis of the entire oligosaccharide fragment. The first enantioselective synthesis of (−)-calicheamicinone is then described. Finally, a novel triggering device for a dynemicin mimic based upon a 2-(phenylsulfonyl)ethylcarbamate isdescribedwhich led to the synthesis of an extremely potent antitumor agent.
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