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Issue 27, 2012
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Total synthesis of indole-3-acetonitrile-4-methoxy-2-C-β-D-glucopyranoside. Proposal for structural revision of the natural product

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Abstract

Indole-3-acetonitrile-4-methoxy-2-C-β-D-glucopyranoside (1), a novel C-glycoside from Isatis indigotica with important cytotoxic activity, has been prepared in ten steps from ethynyl-β-C-glycoside 3 and 2-iodo-3-nitrophenyl acetate 6. Key steps in the synthesis include a Sonogashira coupling and a CuI-mediated indole formation. NMR spectroscopic data for synthetic 1 differs from that reported for the natural product. A revised structure for the natural product, containing an alternate carbohydrate substituent, is proposed.

Graphical abstract: Total synthesis of indole-3-acetonitrile-4-methoxy-2-C-β-d-glucopyranoside. Proposal for structural revision of the natural product

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Publication details

The article was received on 30 Apr 2012, accepted on 30 May 2012 and first published on 01 Jun 2012


Article type: Communication
DOI: 10.1039/C2OB25821H
Citation: Org. Biomol. Chem., 2012,10, 5194-5196
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    Total synthesis of indole-3-acetonitrile-4-methoxy-2-C-β-D-glucopyranoside. Proposal for structural revision of the natural product

    A. Yepremyan and T. G. Minehan, Org. Biomol. Chem., 2012, 10, 5194
    DOI: 10.1039/C2OB25821H

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