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Synthesis of the Maduropeptin Chromophore AglyconContributor(s):Philip Kocienski
Tohoku University, Sendai and The University of Tokyo, Japan
Total Synthesis of the Maduropeptin Chromophore Aglycon
J. Am. Chem. Soc. 2007, 129: 14184-14186
19 March 2008 (online)
macrocyclization - Sonogashira coupling - reductive elimination - enediynes
The target is an extremely labile precursor to an enediyne intermediate whose cycloaromatization to a p-benzyne biradical efficiently cleaves DNA by H-abstraction. The target was constructed from three major fragments A, B, and E.
The cyclization G → H and the penultimate SmI2-mediated reductive elimination were highly diastereoselective. The final deprotection step (7% yield) gave the target as a single atropisomer.