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Synfacts 2008(4): 0329-0329
DOI: 10.1055/s-2008-1042884
DOI: 10.1055/s-2008-1042884
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York
Synthesis of the Maduropeptin Chromophore Aglycon
Contributor(s):Philip KocienskiK. Komano, S. Shimamura, M. Inoue*, M. Hirama*
Tohoku University, Sendai and The University of Tokyo, Japan
Total Synthesis of the Maduropeptin Chromophore Aglycon
J. Am. Chem. Soc. 2007, 129: 14184-14186
Tohoku University, Sendai and The University of Tokyo, Japan
Total Synthesis of the Maduropeptin Chromophore Aglycon
J. Am. Chem. Soc. 2007, 129: 14184-14186
Further Information
Publication History
Publication Date:
19 March 2008 (online)
Key words
macrocyclization - Sonogashira coupling - reductive elimination - enediynes
Significance
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.
Comment
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.