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Syntheses of the plant auxin conjugate 2-O-(indole-3-acetyl)-myo-inositol IAInos

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Abstract

The plant hormone conjugate 2-O-(indole-3-acetyl)-myo-inositol (IAInos) has been selectively prepared for the first time by two routes from myo-inositol. One of the syntheses depended upon the construction of the 3-indoleacetyl group by a Fischer indole synthesis on an unreactive axial hydroxyl group, while the other via a direct acylation of the equatorially orientated hydroxy group created by conformational constraint of the cyclohexane ring. The latter synthesis produced IAInos in 5 steps and 29% overall yield.

Graphical abstract: Syntheses of the plant auxin conjugate 2-O-(indole-3-acetyl)-myo-inositol IAInos

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Publication details

The article was received on 27 Aug 2018, accepted on 12 Sep 2018 and first published on 12 Sep 2018


Article type: Communication
DOI: 10.1039/C8OB02096E
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Syntheses of the plant auxin conjugate 2-O-(indole-3-acetyl)-myo-inositol IAInos

    S. Silva, O. S. Ascenso, E. C. Lourenço, M. Archer, C. D. Maycock and M. R. Ventura, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB02096E

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