The synthesis of ventilone A

MJ Piggott, D Wege

Index: Piggott, Matthew J.; Wege, Dieter Australian Journal of Chemistry, 2000 , vol. 53, # 9 p. 749 - 754

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Citation Number: 20

Abstract

Abstract 2-Amino-3, 6-dimethoxy-4, 5-methylenedioxybenzoic acid (12) was prepared from 1, 4-dimethoxy-2, 3-methylenedioxybenzene (8) via the isatin (11). The benzyne generated from (12) was intercepted with 3-acetyl-2-ethoxy-4-[(4-methoxyphenoxy) methyl] furan (4) to give the naphthol (27), which on treatment with cericammonium nitrate gave the dimethyl ether of ventilone A (29). Demethylation with boron tribromide then affordedventilone A (1) ...