title: Application of the taraxerane-oleanane rearrangement to the synthesis of seco-oleanane triterpenoids from taraxerone.
abstract: 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.
authors.affiliation: a Faculty of Chemistry, VNU University of Science, Vietnam National University , Hanoi, 19 Le Thanh Tong Street, Hanoi , Viet Nam.
authors.forename: Phan Minh
authors.initials: PM
authors.lastname: Giang
authors.forename: Vu
authors.initials: V
authors.lastname: Minh Trang
authors.forename: Phan Tong
authors.initials: PT
authors.lastname: Son
authors.forename: Katsuyoshi
authors.initials: K
authors.lastname: Matsunami
mesh_terms: D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009828:Oleanolic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D000893:Anti-Inflammatory Agents; D000970:Antineoplastic Agents; D007783:Lactones; C413246:oleanane; D009828:Oleanolic Acid; C009379:taraxerone
keywords: 3,4-seco-oleanane; Baeyer–Villiger oxidation; taraxerane–oleanane rearrangement; taraxerone