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

被引：4

作者：

Pillay, Adushan ^{[1
]}

Rousseau, Amanda L. ^{[1
]}

Fernandes, Manuel A. ^{[1
]}

de Koning, Charles B. ^{[1
]}

机构：

[1] Univ Witwatersrand, Sch Chem, Inst Mol Sci, Johannesburg, South Africa

来源：

TETRAHEDRON | 2012年 / 68卷 / 35期

基金：

新加坡国家研究基金会;

关键词：

Marticin; Wacker oxidation; Acetal-containing naphthoquinones; TETRACYCLIC NAPHTHOQUINONE; PENTAS-LONGIFLORA; ISAGARIN; CARDINALIN-3;

D O I：

10.1016/j.tet.2012.06.052

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 LiAlH4 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 LiAlH4 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. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：7116 / 7121

页数：6

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