Syntheses of the plant auxin conjugate 2-O-(indole-3-acetyl)-myo-inositol IAInos. Issue 38 (18th September 2018)

• Record Type: Journal Article
• Authors: Silva, Saúl; Ascenso, Osvaldo S.; Lourenço, Eva C.; Archer, Margarida; Maycock, Christopher D.; Ventura, M. Rita
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 38(2018)
• Page Start: 6860
• Page End: 6864
• Publication Date: 2018-09-18
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob02096e
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : The two first chemical syntheses of IAInos (2- O -(indole-3-acetyl)-myo-inositol), an important plant hormone, are described. 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.