Wacker oxidation methodology for the synthesis of the benzo-fused acetal core of marticin

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• 作者：Adushan Pillay ; Am ; a L. Rousseau ; Manuel A. Fern ; es ; Charles B. de Koning
• 关键词：Marticin ; Wacker oxidation ; Acetal-containing naphthoquinones
• 刊名：Tetrahedron
• 出版年：2012
• 出版时间：2 September, 2012
• 年：2012
• 卷：68
• 期：35
• 页码：7116-7121
• 全文大小：462 K

文摘

Methodology for the synthesis of the benzo-fused acetal core of marticin is described in this paper. Condensation of readily available 1-(2-allyl-3,6-dimethoxyphenyl)ethanone with diethyl oxalate under Claisen condensation conditions furnished (Z)-ethyl 4-(2-allyl-3,6-dimethoxyphenyl)-2-hydroxy-4-oxobut-2-enoate. Treatment of this with LiAlHb>4b> resulted in the formation of the diol, 1-(2-allyl-3,6-dimethoxyphenyl)-3,4-dihydroxybutan-1-one. Conversion of primary alcohol of the diol into the TBDMS ether followed by further reaction with LiAlHb>4b> and exposure to Wacker oxidation conditions resulted in the formation of (3,6-dimethoxy-9-methyl-10,13-dioxatricyclo[7.3.1.0^2,7]trideca-2,4,6-trien-11-yl)methanol, the core of marticin.