文献类型：期刊文献

中文题名：Formal Synthesis of Dydrogesterone:A Milder Dearomatization Strategy

英文题名：地屈孕酮的形式合成:一种温和的去芳构化策略

作者：Yao Hongmiao[2];Wang Shaodong[2];Yuan Xinxin[2];Zeng Qianding[1];Jiang Hai[3];Zou Yiyong[3];Ren Jiangmeng[2];Zhang Yusong[4];Zeng Bu-Bing[1]

机构：[1]Shanghai Key Laboratory of Chemical Biology,School of Pharmacy,East China University of Science and Technology,Shanghai 200237;[2]School of Pharmacy,East China University of Science and Technology,Shanghai 200237;[3]Taizhou Xianju Pharmaceutical Co.Ltd.,Taizhou,Zhejiang 317016;[4]Zhejiang Xianju Pharmaceutical Co.Ltd.,Taizhou,Zhejiang 317306

年份：2025

卷号：45

期号：9

起止页码：3478

中文期刊名：有机化学

外文期刊名：Chinese Journal of Organic Chemistry

收录：;北大核心:【北大核心2023】；

语种：英文

中文关键词：dydrogesterone;dearomatization;steroid;Heck coupling

外文关键词：地屈孕酮;去芳构化;甾体;Heck偶联

摘要：A dearomatization strategy using dicetolic acid(6)as the starting material to synthesize the core intermediate(10R,13S,14S)-10,13-dimethyl-7,10,11,12,13,14,15,16-octahydro-3H-cyclopenta[a]phenanthrene-3,17(6H)-dione(20)for the formal synthesis of dydrogesterone is presented,achieving a total yield of 21%over nine steps.This approach features an environmentally friendly carbonyl protection strategy and efficient Heck coupling,while avoiding harsh conditions and hazardous reagents throughout the entire process.
开发了一种以3-((3a S,4S,7a S)-7a-甲基-1,5-二氧代八氢-1H-茚-4-基)丙酸(6)为起始原料的去芳构化策略,用于地屈孕酮的形式合成.该策略通过9个步骤,以21%的总收率获得地屈孕酮的核心中间体(10R,13S,14S)-10,13-二甲基-7,10,11,12,13,14,15,16-八氢-3H-环戊[a]菲-3,17(6H)-二酮(20).该策略的特点在于采用了环境友好的羰基保护策略和高效的Heck偶联反应,同时在整个过程中避免了苛刻条件和有害试剂的使用.