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Citation: LIU Yan, YANG Haijun, LI Chunling, LIU Cailin, YANG Junxiao. Synthesis and Oxidation of Acetoxy-Substituted Triene of Oleanolic Acid[J]. Chinese Journal of Applied Chemistry, ;2011, 28(2): 182-187. doi: 10.3724/SP.J.1095.2011.00314 shu

Synthesis and Oxidation of Acetoxy-Substituted Triene of Oleanolic Acid

1.
College of Materials Science and Engineering, Southwest University of Science and Technology, Mianyang 621010

Corresponding author: YANG Haijun,
Received Date: 26 May 2010
Available Online: 20 July 2010
Fund Project: 国家自然科学基金(20802059) (20802059)西南科技大学博士研究基金(07zx7129)资助项目 (07zx7129)

Acetoxy-substituted triene(6) was synthesized from oleanolic acid(1) via methyl esterification of 17-carboxylic acid,benzoylation of 3-hydroxy,oxidation of 12-double bond by O₃,dehydrogenation with Br₂/HBr,enol acetylation of carbonyl group,and ring-C opening under UV light.Oxidations of compound 6 with different oxidants such as O₃,meta-cholorperoxybenzoic acid(mCPBA),H₂O₂,t-BuOOH and Na₂S₂O₈,yield decalin-type chiral synthons,epoxides,and/or lactone of oleanolic acid derivatives.
- oleanolic acid,
- triene,
- synthesis,
- oxidation
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