Stereospecific Oxidation of Diacetoxyheterobetulin with Ozone and Dimethyldioxirane-Reference-Cited by-同舟云学术

Stereospecific Oxidation of Diacetoxyheterobetulin with Ozone and Dimethyldioxirane

Published:2016-04 Issue:4 Volume:11 Page:1934578X1601100
ISSN:1934-578X
Container-title:Natural Product Communications
language:en
Short-container-title:Natural Product Communications

Author:

Khusnutdinova El'mira F.¹,Medvedeva Natalya I.¹,Kazakov Dmitri V.¹,Kukovinets Olga S.¹,Lobov Alexander N.¹,Suponitsky Kirill Yu.²,Kazakova Oxana B.¹

Affiliation:

1. Ufa Institute of Chemistry, Russian Academy of Sciences, 71 Prospect Oktyabrya, 450054, Ufa, Russian Federation

2. A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St, V-334, 119991, GSP–1, Moscow, Russian Federation

Abstract

Stereospecific oxidation of diacetoxyheterobetulin with ozone and dimethyldioxirane led to 3β,28-diacetoxy-18α,19pH-urs-20α,21α-epoxide with yields of 79% and 87%, respectively. Oxidation with ozone was not selective and gave two minor products containing 21α-hydroxy-20(30)-ene and 21α-hydroxy-20β,28-epoxy- fragments in ring E. The structures of 3β,28-diacetoxy-18α,19pH-urs-20α,21α-epoxide and 3β-diacetoxy-21α-hydroxy-20β,28-epoxy-18α,19βH-ursane were confirmed by X-ray analysis for the first time.

Publisher

SAGE Publications

Subject

Complementary and alternative medicine,Plant Science,Drug Discovery,Pharmacology,General Medicine

Link

http://journals.sagepub.com/doi/pdf/10.1177/1934578X1601100407

Reference23 articles.

1. Synthesis, biology and clinical significance of pentacyclic triterpenes: a multi-target approach to prevention and treatment of metabolic and vascular diseases

2. Efficient oxidation of oleanolic acid derivatives using magnesium bis(monoperoxyphthalate) hexahydrate (MMPP): A convenient 2-step procedure towards 12-oxo-28-carboxylic acid derivatives

3. Efficient and Scalable Synthesis of Bardoxolone Methyl (CDDO-methyl Ester)

4. Double Bond Migration on the 22(17.RAR.28)abeo-Lupane Skeleton.

5. Reactions of Activated Lupane Oxo-Compounds with Diazomethane: An Approach to New Derivatives of Cytotoxic Triterpenes

Cited by 2 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Diastereoselective Synthesis of Triterpenoid 1,2,4-Trioxolanes by Griesbaum Co-ozonolysis;Journal of Natural Products;2019-09-06

2. Synthesis of new A-conjugated Quinolone and Spiroindole Dammaranes by the Ozonolysis of 2,3-Indolodipterocarpol;Natural Product Communications;2018-05