Synthesis and Oxidation of Acetoxy-Substituted Triene of Oleanolic Acid

doi:10.3724/SP.J.1095.2011.00314

Chinese Journal of Applied Chemistry ›› 2011, Vol. 28 ›› Issue (02): 182-187.DOI: 10.3724/SP.J.1095.2011.00314

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Synthesis and Oxidation of Acetoxy-Substituted Triene of Oleanolic Acid

LIU Yan, YANG Hai-Jun^*, LI Chun-Ling, LIU Cai-Lin, YANG Jun-Xiao

(College of Materials Science and Engineering,Southwest University of Science and Technology,Mianyang 621010)

Received:2010-05-26 Revised:2010-07-09 Published:2011-02-10 Online:2011-02-10
Contact: Yang haijun

Abstract

Abstract:

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.

Key words: oleanolic acid, triene, synthesis, oxidation

CLC Number:

O629

LIU Yan, YANG Hai-Jun*, LI Chun-Ling, LIU Cai-Lin, YANG Jun-Xiao. Synthesis and Oxidation of Acetoxy-Substituted Triene of Oleanolic Acid[J]. Chinese Journal of Applied Chemistry, 2011, 28(02): 182-187.

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Synthesis and Oxidation of Acetoxy-Substituted Triene of Oleanolic Acid

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