Synthesis of triterpenoid-based 1,2,4-trioxolanes and 1,2,4-dioxazolidines by ozonolysis of allobetulin derivatives

被引：38
|
作者：
Kazakova, Oxana B. [1 ]
Kazakov, Dmitri V. [1 ]
Yamansarov, Emil Yu. [1 ]
Medvedeva, Natal'ya I. [1 ]
Tolstikov, Genrikh A. [1 ]
Suponitsky, Kyrill Yu. [2 ]
Arkhipov, Dmitri E. [2 ]
机构：
[1] Russian Acad Sci, Ufa Res Ctr, Inst Organ Chem, Ufa 450054, Russia
[2] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 09期
基金：
俄罗斯基础研究基金会;
关键词：
Natural products; Triterpenoids; Betulin; Antimalarials; Peroxides; 1,2,4-Trioxolanes; 1,2,4-Dioxazolidines; Ozonolysis; ANTIMALARIAL ACTIVITY; QINGHAOSU ARTEMISININ; HEME ALKYLATION; BETULINIC ACID; PEROXIDES; DRUG; TRIOXANES;
D O I：
10.1016/j.tetlet.2010.12.047
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Oxidation of allobetulin derivatives with ozone results in good isolated yields of 1,2,4-trioxolanes and stable 1,2,4-dioxazolidines. Individual 3R,5R and 3S,5S diastereoisomers of allobetulin secondary ozonides were isolated and their structures confirmed by X-ray crystallographic analysis. Remarkable diastereoselectivity with formation of only the (3S,5S)-configured peroxides was observed during the oxidation of 1,5-di-O-methoxyoximinoallobetulin to dioxazolidines. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：976 / 979
页数：4
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