Issue 38, 2018

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

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

Supplementary files

Article information

Article type
Communication
Submitted
27 ኦገስ 2018
Accepted
12 ሴፕቴ 2018
First published
12 ሴፕቴ 2018

Org. Biomol. Chem., 2018,16, 6860-6864

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, 16, 6860 DOI: 10.1039/C8OB02096E

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