Application of the taraxerane-oleanane rearrangement to the synthesis of seco-oleanane triterpenoids from taraxerone

Synthetic oleananes and seco-oleananes form a group of promising anti-inflammatory and cancer chemopreventive agents with an excellent safety profile. These compounds are usually prepared by semi-synthesis from natural oleanane triterpenoids. Since a taraxer-14-ene was reported to be rearranged into...

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Bibliographic Details
Published in:Natural product research 2015-01, Vol.29 (1), p.64-69
Main Authors: Giang, Phan Minh, Minh Trang, Vu, Son, Phan Tong, Matsunami, Katsuyoshi
Format: Article
Language:English
Subjects:
3,4-seco-oleanane
Anti-Inflammatory Agents - chemical synthesis
Anti-Inflammatory Agents - chemistry
Anti-Inflammatory Agents - pharmacology
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Baeyer-Villiger oxidation
Lactones - chemical synthesis
Lactones - chemistry
Molecular Structure
Oleanolic Acid - analogs & derivatives
Oleanolic Acid - chemical synthesis
Oleanolic Acid - chemistry
Oleanolic Acid - pharmacology
Structure-Activity Relationship
taraxerane-oleanane rearrangement
taraxerone
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Summary:Synthetic oleananes and seco-oleananes form a group of promising anti-inflammatory and cancer chemopreventive agents with an excellent safety profile. These compounds are usually prepared by semi-synthesis from natural oleanane triterpenoids. Since a taraxer-14-ene was reported to be rearranged into an olean-12-ene under mild reaction conditions, a rapid synthesis of seco-oleananes from taraxerone, which is a readily available starting material, was explored by us. Treatment of taraxerone with m-chloroperoxybenzoic acid gave 14,15-epoxy lactones, which underwent the taraxerane-oleanane rearrangement leading to new seco-oleanane triterpenoids.
ISSN:1478-6419
1478-6427
DOI:10.1080/14786419.2014.958737