Takeuchi Hironori, Ueda Yoshihiro, Furuta Takumi, Kawabata Takeo
Institute for Chemical Research, Kyoto University.
Chem Pharm Bull (Tokyo). 2017;65(1):25-32. doi: 10.1248/cpb.c16-00436.
A short-step total synthesis of the natural glycosides pterocarinin C and tellimagrandin II (eugeniin) has been performed by sequential and site-selective functionalization of free hydroxy groups of unprotected D-glucose. The key reactions are β-selective glycosidation of a gallic acid derivative using unprotected D-glucose as a glycosyl donor and catalyst-controlled site-selective introduction of a galloyl group into the inherently less reactive hydroxy group of the glucoside.
通过对未保护的D-葡萄糖的游离羟基进行连续和位点选择性官能化，实现了天然糖苷紫檀素C和tellimagrandin II（诃子鞣质）的短步骤全合成。关键反应包括使用未保护的D-葡萄糖作为糖基供体对没食子酸衍生物进行β-选择性糖苷化，以及催化剂控制的将没食子酰基位点选择性引入糖苷中固有反应性较低的羟基。
