Synthesis of pennogenin utilizing the intact skeleton of diosgenin  

作　　者：TIAN Weisheng XU Qihai CHEN Ling ZHAO Chunfeng 

机构地区：[1]Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

出　　处：《Science China Chemistry》2004年第2期142-144,共3页中国科学（化学英文版）

基　　金：This work was supported by the National Natural Science Foundation of China(Grant No.20372078).

摘　　要：The first synthesis of pennogenin, an aglycone of bioactive components of Chinese traditional medicine named Chonglou(Paris), starting from diosgenin, has been reported, which displays a new strategy of utilizing the resource compounds. According to this new strategy, the full and rational utilization of the intact skeleton and functional groups of starting material has been realized in the conversion of diosgenin to pennogenin. The key step for synthesis of pen-nogenin is the regioselective transformation of cholest-5-en-16,22-dion-3,26-diol to cholest- 5,16-dien-22-on-3,26-diol, which can be used to synthesize other bioactive steroids such as cephalostatin and OSW-1.The first synthesis of pennogenin, an aglycone of bioactive components of Chinese traditional medicine named “Chonglou”(Paris), starting from diosgenin, has been reported, which displays a new strategy of utilizing the resource compounds. According to this new strategy, the full and rational utilization of the intact skeleton and functional groups of starting material has been realized in the conversion of diosgenin to pennogenin. The key step for synthesis of pennogenin is the regioselective transformation of cholest-5-en-16,22-dion-3,26-diol to cholest-5,16-dien-22-on-3,26-diol, which can be used to synthesize other bioactive steroids such as cephalostatin and OSW-1.

关 键 词：pennogenin  Chonglou  diosgenin  aglycone  synthesis  ATOM economy. 

分 类 号：O6[理学—化学]