%0 Journal Article %J RSC Advances %D 2014 %T Dimethyl homophthalates to naphthopyrans: the total synthesis of arnottin I and the formal synthesis of (-)-arnottin II %A Jangir, Ravi %A N. P. Argade %X

A simple and efficient 3-step synthetic protocol has been reported for dimethyl homophthalates to naphthopyrans. Starting from dimethyl 2,3-dimethoxyhomophthalate, a practical synthesis of arnottin I has been described via a base catalyzed mono-alkylation, the selective hydrolysis of an aliphatic ester moiety, two consecutive intramolecular cyclizations and an oxidative aromatization pathway with a very good overall yield. The involved intramolecular acylation followed by an associated enolative lactonization was the decisive step. The synthesis of dihydroarnottin I also completes the formal synthesis of (-)-arnottin II.

%B RSC Advances %I ROYAL SOC CHEMISTRY %C THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND %V 4 %P 5531-5535 %8 JAN %G eng %N 11 %9 Article %3

Foreign

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3.289

%R 10.1039/c3ra45312j