Synfacts 2008(4): 0329-0329  
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 Kocienski
K. 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  
Further Information

Publication History

Publication Date:
19 March 2008 (online)


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.