Oxidation of hecogenin and diosgenin derivatives with dimethyldioxirane

被引:0
|
作者
Zhu, BK
Zhang, HB
Zhang, YS
Zhong, HM
Liu, JP [1 ]
机构
[1] Yunnan Univ, Ctr Adv Studies Med & Organ Chem, Sch Pharm, Kunming 650091, Peoples R China
[2] Qingdao Sci & Tech Univ, Sch Chem, Qingdao 266042, Peoples R China
关键词
oxidation; dimethyldioxirane; hecogenin; diosgenin; derivative;
D O I
暂无
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Diacetyl derivative of hecogenin 1 was oxidized to unsaturated ketone 5 via allylic alcohol 3 when it reacted with dimethyldioxirane (DMDO). The structure of 3 was confirmed by X-ray crystal analysis and the highly regioselectivity of DMDO to different olefin bonds was also observed when diosgenin derivative 6 was treated with DMDO.
引用
收藏
页码:143 / 146
页数:4
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