论文部分内容阅读
真菌聚酮(cytosporone B,Csn-B)具有多种生物活性,是研究生物过程的重要小分子探针,其高效合成备受关注.本研究以商品3,5-二羟基苯乙酮为原料,苄基保护羟基得到3,5-二苄氧基苯乙酮,然后与硫粉和吗啡啉进行Willgerodt-Kindler反应得到3,5-二苄氧基苯乙硫酰胺,一锅煮水解该酰胺得到关键中间体3,5-二苄氧基苯乙酸;然后经酯化、傅克酰基化和脱除苄基,分别以5步反应得到Csn-B(总产率68.8%)或secocurvularin(总收率67.3%);Csn-B经水解得到cytosporone A(Csn-A),总产率65.3%;Csn-B经还原环合得到cytosporone C(Csn-C),总产率64.0%.该合成方法步骤少、产率高,原料廉价,适合Csn-B的大量制备.
Fungal polyketides (Csn-B) have many biological activities and are important small molecule probes for studying biological processes, and their efficient synthesis has attracted much attention.In this study, 3,5-dihydroxyacetophenone , The benzyl group is protected to give 3,5-dibenzyloxyacetophenone, which is then Willgerodt-Kindler reacted with sulfur powder and morpholine to give 3,5-dibenzyloxyphenylacetamide, which is key to the one-pot hydrolysis of the amide The intermediate 3,5-dibenzyloxyphenylacetic acid was then esterified, Friedel-acylated and benzyl was removed to give Csn-B (68.8% overall yield) or secocurvularin (total yield 67.3%). Cytosporone A (Csn-A) was obtained by hydrolysis of Csn-B with a total yield of 65.3%. Cytosporone C (Csn-C) Less, high yield, cheap raw materials, suitable for a large number of Csn-B preparation.