1-(5,7-二羟基-2,2-二甲基苯并吡喃)-3-(2,2-二甲基苯并吡喃)双氢查尔酮的首次全合成

标题化合物是从Metrodorea stipularis树枝中提取出来的,此化合物具有抗南美洲锥虫病、抗疟疾、抗肿瘤等药理作用。以廉价的2,4,6-三羟基苯乙酮、4-羟基苯甲醛为原料,经吡喃环化、苄基保护酚羟基、羟醛缩合和Pd-C/H2还原不饱和双键及脱保护基,完成天然产物1-(5,7-二羟基-2,2-二甲基苯并吡喃)-3-(2,2-二甲基苯并吡喃)双氢查尔酮的全合成。所有新化合物的结构均经过NMR、IR、HR-MS确认。初步生物活性实验结果表明,1-(5,7-二羟基-2,2-二甲基苯并吡喃)-3-(2,2-二甲基苯并吡喃)双氢查尔酮对大肠杆菌的最小抑菌浓度为32μg/mL。

Total Synthesis of 1-(5,7-Dihydroxy-2,2-dimethylchroman-6-yi)-3-(2,2-dimethylchroman-6-yl) propan-1-one

1-(5,7-Dihydroxy-2,2-dimethylchroman-6-yl)-3-(2,2-dimethylchroman-6-yl) propan-1-one was isolated from stem of Metrodorea stipularis.This compound had the pharmacological effect on antichagastic,antimalarial and antitumoral.Herein,The total synthetic of 1-(5,7-dihydroxy-2,2-dimethylchroman-6-yl)-3-(2,2-dimethylchroman-6-yl) propan-l-one was achieved through benzopyran,protection of phenolic hydroxyl group,aldol condensation,Pd-C/H2 reduction and deprotection starting from cheap 2,4,6-trihydroxyacetophenone and 4-hydroxybenzaldehyde.The structures of all new compounds were confirmed by NMR,IR and HRMS.The preliminary bioassay showed that the MIC of the compound with Esherichia coli was 32 μg/mL.