心红菌素3的单体通气醌L的合成。
The synthesis of ventiloquinone L, the monomer of cardinalin 3.
作者信息
Mmutlane Edwin M, Michael Joseph P, Green Ivan R, De Koning Charles B
机构信息
Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, PO Wits, 2050, South Africa.
出版信息
Org Biomol Chem. 2004 Sep 7;2(17):2461-70. doi: 10.1039/B407208A. Epub 2004 Aug 2.
Readily available ethyl-4-acetoxy-6,8-dimethoxynaphthalene-2-carboxylate was converted into 1-[3-allyl-4-(benzyloxy)-6,8-dimethoxy-2-naphthyl)-1-ethanol in seven steps. Subjection of this compound to Wacker oxidation conditions provided 5-benzyloxy-7,9-dimethoxy-1,3-dimethyl-1H-benzo[g]isochromene in good yield. Hydrogenation of the isochromene afforded (+/-)-cis-7,9-dimethoxy-1,3-dimethyl-1H-benzo[g]isochroman-5-ol as the major product, which was readily converted into ventiloquinone L.
容易获得的4-乙酰氧基-6,8-二甲氧基萘-2-羧酸乙酯经过七步反应转化为1-[3-烯丙基-4-(苄氧基)-6,8-二甲氧基-2-萘基]-1-乙醇。将该化合物置于瓦克氧化条件下，以良好的产率得到5-苄氧基-7,9-二甲氧基-1,3-二甲基-1H-苯并[g]异色烯。异色烯氢化得到(±)-顺式-7,9-二甲氧基-1,3-二甲基-1H-苯并[g]异色满-5-醇作为主要产物，该产物很容易转化为通气醌L。
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