摘要
提供了一种将剑麻皂甙元降解产物孕甾三醇转化为孕甾-16-烯-3S,20S-二醇二乙酸酯(Ⅱ)的高效合成方法,并重新考察了其钯催化反应。研究发现亲核取代反应和消除反应互相竞争,在醋酸钯催化下,C-20亲核取代产物Ⅲ为主产物,而在四(三苯基膦)合钯催化下,则主要生成C-20消除产物(Ⅴ)。这些结果不仅为甾体药物和生物活性天然甾体化合物合成提供了新的合成中间体,也为进一步合理利用剑麻皂甙元资源提供了新思路。
Pregnana-3,16,20-triol was efficiently transformed into pregn-16-ene-3S, 20S-diol diacetate （ Ⅱ ）. And then the Pd-catalyzed reaction was reinvestigated. The research results showed that the nueleophilic product （ Ⅲ） is predominant in the presence of Pd（ OAc）2 while the elimination product （ Ⅴ ） is dominated in the presence of [ PPh3 ]4Pd. These results not only provided new synthetic intermediates for the syntheses of steroidal drugs and natural steroids, but also presented the new routes of utilization of tigogenin.
出处
《应用化工》
CAS
CSCD
2009年第5期640-644,647,共6页
Applied Chemical Industry
基金
上海市教育委员会科研创新项目(09Y164,08YZ70)
上海师范大学一般科研项目(SK200721)
上海师范大学前瞻性科研项目(DYL200903)
