Issue 38, 2018
From the journal:

Organic & Biomolecular Chemistry

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

Saúl Silva,a   Osvaldo S. Ascenso,a   Eva C. Lourenço,a   Margarida Archer,b   Christopher D. Maycockbc  and  M. Rita Ventura ORCID logo *b  

* Corresponding authors

a Extremochem Lda, Rua Ivone Silva, 6, 4° piso, 1050-124 Lisboa, Portugal

b Instituto de Tecnologia Química e Biológica António Xavier, Universidade Nova de Lisboa, Av. da República, 2780-157 Oeiras, Portugal
E-mail: rventura@itqb.unl.pt

c Faculdade de Ciências da Universidade de Lisboa, Departamento de Química e Bioquímica, 1749-016 Lisboa, Portugal

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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Article information

DOI
https://doi.org/10.1039/C8OB02096E
Article type
Communication
Submitted
27 Aug 2018
Accepted
12 Sep 2018
First published
12 Sep 2018

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

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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, 16, 6860 DOI: 10.1039/C8OB02096E

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