Preparative routes to spiroacetals derived from chroman-4-one (2,3-dihydro-4H-1-benzopyran-4-one)
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Add time:07/21/2019 Source:sciencedirect.com
Methyl 2-(4-hydroxybutyl)-4-oxo-4H-1-benzopyran-3-carboxylate 6 is transformed into the spiroacetals 13 and 14 (ratio 5:1) via treatment with iodomethane/potassium carbonate, the process involving sequential intramolecular conjugate addition and enolate alkylation. The 2,3-epoxide 7 derived from 6 undergoes spirocyclisation to the hydroxyesters 16 and 17 upon treatment with acids. The structures of 13 and 16 were confirmed by X-ray crystallography.
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