Giang Phan Minh, Minh Trang Vu, Son Phan Tong, Matsunami Katsuyoshi
a Faculty of Chemistry, VNU University of Science, Vietnam National University , Hanoi, 19 Le Thanh Tong Street, Hanoi , Viet Nam.
Nat Prod Res. 2015;29(1):64-9. doi: 10.1080/14786419.2014.958737. Epub 2014 Sep 15.
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.
合成齐墩果烷和裂环齐墩果烷构成了一类有前景的抗炎和癌症化学预防剂，具有出色的安全性。这些化合物通常通过从天然齐墩果烷三萜类化合物进行半合成来制备。由于据报道蒲公英赛-14-烯在温和反应条件下可重排为齐墩果-12-烯，我们探索了从易于获得的起始原料蒲公英赛酮快速合成裂环齐墩果烷的方法。用间氯过氧苯甲酸处理蒲公英赛酮得到14,15-环氧内酯，其经历了蒲公英烷-齐墩果烷重排，从而产生新的裂环齐墩果烷三萜类化合物。
