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  • Title: Diversity-oriented synthesis of 1-hydroxy-2,4-benzodioates by regioselective [3+3] cyclocondensations of 1,3-bis(silyloxy)-1,3-butadienes with 3-alkoxy- and 3-silyloxy-2-alkoxycarbonyl-2-en-1-ones.
    Author: Shkoor M, Riahi A, Fatunsin O, Hussain I, Yawer MA, Lubbe M, Reim S, Reinke H, Fischer C, Langer P.
    Journal: Org Biomol Chem; 2009 May 21; 7(10):2182-6. PubMed ID: 19421458.
    Abstract:
    1-Hydroxy-3,5-dimethyl-2,4-benzodioates (4-hydroxyisophthalates) were prepared by [3+3] cyclocondensation of 1,3-bis(silyloxy)-1,3-butadienes with 3-ethoxycarbonyl-4-trimethylsilyloxy-3-penten-2-one which is synthesized from (symmetrical) ethyl 2-acetylacetoacetate. The [3+3] cyclization of 1,3-bis(silyloxy)-1,3-butadienes with 3-alkoxy-2-alkoxycarbonyl-2-en-1-ones, readily available by reaction of beta-ketoesters with trialkyl orthoformiates, provide a convenient and regioselective approach to a great variety of 3-substituted 1-hydroxy-2,4-benzodioates that are not readily available by other methods.
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