The synthesis of ventiloquinone L, the monomer of cardinalin 3

…, JP Michael, IR Green, CB de Koning

Index: Mmutlane, Edwin M.; Michael, Joseph P.; Green, Ivan R.; De Koning, Charles B. Organic and Biomolecular Chemistry, 2004 , vol. 2, # 17 p. 2461 - 2470

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Citation Number: 27

Abstract

Readily available ethyl-4-acetoxy-6, 8-dimethoxynaphthalene-2-carboxylate 27 was converted into 1-[3-allyl-4-(benzyloxy)-6, 8-dimethoxy-2-naphthyl)-1-ethanol 31 in seven steps. Subjection of this compound to Wacker oxidation conditions provided 5-benzyloxy-7, 9-dimethoxy-1, 3-dimethyl-1H-benzo [g] isochromene 32 in good yield. Hydrogenation of the isochromene afforded (±)-cis-7, 9-dimethoxy-1, 3-dimethyl-1H-benzo [g] isochroman-5-ol ...