Chemistry of steroidal saponins as natural resource compounds
10.11665/j.issn.1000-5048.20190103
- VernacularTitle:天然资源型化合物甾体皂苷元的化学研究
- Author:
Weisheng TIAN
1
Author Information
1. 中国科学院上海有机化学研究所
- Publication Type:Journal Article
- Keywords:
resources chemistry;
steroidal saponins;
natural products;
chiral reagents;
asymmetric synthesis
- From:
Journal of China Pharmaceutical University
2019;50(1):19-32
- CountryChina
- Language:Chinese
-
Abstract:
This article briefly summarizes our group′s systematic studies on the resource chemistry of steroidal sapogenins. Steroidal sapogenins are an important class of natural compounds, which could be utilized to synthesize various steroidal drugs. In order to achieve their efficient, clean and atom-economical utilization, our research group systematically investigated the oxidative degradation reaction of steroidal sapogenins. By employing 30% H2O2 as the oxidant, pseudo-sapogenins and sapogenins could be oxidized to the corresponding pregnenolone, pregnane-3β, 16, 20-triol, steroidal 22-lactone, as well as a series of bifunctional reagents with chiral methyl group. These oxidative degradation products have been applied to the synthesis of steroidal drugs, biologically active natural steroidal molecules and non-steroid functional chiral molecules. Furthermore, we explored the bromination-ring opening, amination-ring opening and bromolactonization reactions of the spiroketal moiety, which provides new strategies and methods in the utilization of their intact skeleton to the efficient syntheses of active components of traditional Chinese medicines with the cholesterol skeleton, as well as biologically active steroidal natural products.
