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Issue 41, 2014
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A one-pot multicomponent coupling/cyclization for natural product herbicide (±)-thaxtomin A

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Abstract

Herbicide (±)-thaxtomin A has been synthesized in a one-pot process with a 32% isolated yield. A multicomponent coupling reaction was utilized to prepare in situ a dipeptide precursor which then sequentially underwent an alkaline mediated keto-amide cyclization to provide the target molecule. Adjustment of diastereoselectivity was achieved using microwave-induced irradiation. The approach incorporates atom economy and reaction efficiency and allows for facile library development.

Graphical abstract: A one-pot multicomponent coupling/cyclization for natural product herbicide (±)-thaxtomin A

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Publication details

The article was received on 04 Jun 2014, accepted on 17 Jul 2014 and first published on 24 Jul 2014


Article type: Communication
DOI: 10.1039/C4OB01148A
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2014,12, 8125-8127
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    A one-pot multicomponent coupling/cyclization for natural product herbicide (±)-thaxtomin A

    J. P. Bourgault, A. R. Maddirala and P. R. Andreana, Org. Biomol. Chem., 2014, 12, 8125
    DOI: 10.1039/C4OB01148A

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