天然产物胭木二酮的全合成

Total Synthesis of Natural Product Wrightiadione

胭木二酮作为一种同时含有异黄酮和茚酮结构的天然产物,其全合成方法的路线设计对于相关天然产物的制备和药物研发领域具有相当重要的意义。以廉价易得的2-羟基苯乙酮为起始原料,经过缩合环化,碘代反应和铃木反应设计并合成了底物2-甲基-异黄酮(4)。在二氧化锡和三氟甲磺酸铜条件下通过氧化/傅克反应/芳构化一锅法成功制备了胭木二酮,4步反应总产率为49%。所有化合物的结构都经过^(1)H NMR、^(13)C NMR和HR-MS表征确认。该合成方法具有起始原料简单易得,合成线路短,产率高等优点。

Wrightiadione is a natural product containing both isoflavone and indanone structures.The design of total synthesis route is of great significance for the preparation of related natural products and drug development.The 2-methyl-isoflavone(4)was designed and synthesized by condensation cyclization,iodination reaction and Suzuki reaction starting from cheap and accessible material 2-hydroxyacetophenone.Wrightiadione was successfully prepared by one-pot oxidation/Friedel-Crafts reaction/aromatization under the conditions of SeO_(2) and Cu(OTf)_(2).The total synthesis route was achieved through four steps with yield 49%.All structures of compounds were confirmed by ^(1)H NMR、^(13)C NMR、HR-MS.This work provides a new strategy to generate wrightiadione with a facile and cost-effective method.