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

Research output: Contribution to journalArticle

1 Citation (Scopus)

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 languageEnglish
Pages (from-to)6860-6864
Number of pages5
JournalOrganic and Biomolecular Chemistry
Volume16
Issue number38
DOIs
Publication statusPublished - 1 Jan 2018

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