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Issue 24, 2014
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A versatile synthesis of “tafuramycin A”: a potent anticancer and parasite attenuating agent

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Abstract

An improved and versatile synthesis of tafuramycin A, a potent anticancer and parasite-attenuating agent, is reported. The three major improvements that optimized yield, simplified purification and allowed the synthesis of more versatile duocarmycin analogues are: a first-time reported regioselective bromination using DMAP as catalyst; the control of the aryl radical alkene cyclization step to prevent the dechlorination side reaction; and the design of a new protection/deprotection method to avoid furan double bond reduction during the classical O-benzyl deprotection in the final step. This alternative protection/deprotection strategy provides ready access to duocarmycin seco-analogues that carry labile functionalities under reducing reaction conditions. Tafuramycin A (3) was prepared in either 8 steps from intermediate 6 or 7 steps from intermediate 17 in 52% or 37% yield respectively. Our strategy provides a significant improvement on the original procedure (11% overall yield) and greater versatility for analogue development.

Graphical abstract: A versatile synthesis of “tafuramycin A”: a potent anticancer and parasite attenuating agent

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Publication details

The article was received on 17 Mar 2014, accepted on 06 May 2014 and first published on 06 May 2014


Article type: Paper
DOI: 10.1039/C4OB00842A
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2014,12, 4260-4264
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    A versatile synthesis of “tafuramycin A”: a potent anticancer and parasite attenuating agent

    I. M. El-Deeb, F. J. Rose, P. C. Healy and M. von Itzstein, Org. Biomol. Chem., 2014, 12, 4260
    DOI: 10.1039/C4OB00842A

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