The National Engineering Research Centre for Carbohydrate Synthesis, Jiangxi Normal University , Nanchang 330022, China.
Org Lett. 2016 Mar 18;18(6):1294-7. doi: 10.1021/acs.orglett.6b00216. Epub 2016 Feb 26.
By taking full advantage of the mild promotion conditions of an ortho-alkynylbenzoate glycosylation protocol, a highly efficient approach to construct the challenging (epi)-podophyllotoxin 4-O-glycosidic linkages was devised under the activation of a catalytic amount of a Au(I) complex. The novel method enjoys a quite broad substrate scope in terms of both glycosyl donors and podophyllotoxin derivative acceptors, providing the desired glycosides in excellent yields. Based on the new approach, concise syntheses of clinically used anticancer reagents etoposide and teniposide were accomplished, and the overall yields counting from easily available starting materials could reach as high as 18% and 9%, respectively.
充分利用邻炔基苯甲酸酯糖基化反应条件温和的优势，在催化量的金（I）配合物的活化下，设计了一种高效的方法来构建具有挑战性的（表）鬼臼毒素 4-O-糖苷键。该新方法在糖基供体和鬼臼毒素衍生物受体两方面都具有相当广泛的底物范围，以优异的收率得到所需的糖苷。基于新方法，完成了临床上使用的抗癌试剂依托泊苷和替尼泊苷的简洁合成，从易得的起始原料计算，总收率分别高达 18%和 9%。
