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

Saúl Silva; Osvaldo S. Ascenso; Eva C. Lourenço; Margarida Archer; Christopher D. Maycock; M. Rita Ventura

doi:10.1039/C8OB02096E

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

Saúl Silva, Osvaldo S. Ascenso, Eva C. Lourenço, Margarida Archer, Christopher D. Maycock, M. Rita Ventura

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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.

Original language	English
Pages (from-to)	6860-6864
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	16
Issue number	38
DOIs	https://doi.org/10.1039/C8OB02096E
Publication status	Published - 1 Jan 2018

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title = "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.",

author = "Sa{\'u}l Silva and Ascenso, {Osvaldo S.} and Louren{\c c}o, {Eva C.} and Margarida Archer and Maycock, {Christopher D.} and Ventura, {M. Rita}",

year = "2018",

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AU - Silva, Saúl

AU - Ascenso, Osvaldo S.

AU - Lourenço, Eva C.

AU - Archer, Margarida

AU - Maycock, Christopher D.

AU - Ventura, M. Rita

PY - 2018/1/1

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N2 - 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.

AB - 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.

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JF - Organic & Biomolecular Chemistry

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