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 | |
| Publication status | Published - 1 Jan 2018 |
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Silva, S., Ascenso, O. S., Lourenço, E. C., Archer, M., Maycock, C. D., & Ventura, M. R. (2018). Syntheses of the plant auxin conjugate 2-O-(indole-3-acetyl)-myo-inositol IAInos. Organic and Biomolecular Chemistry, 16(38), 6860-6864. https://doi.org/10.1039/C8OB02096E