Targeted synthesis of macrodiolides containing bis-methylene-separated Z-double bonds and their antitumor activity in vitro
作者:Vladimir A. D'yakonov、Ilgiz I. Islamov、Lilya U. Dzhemileva、Elvina M. Khusainova、Milyausha M. Yunusbaeva、Usein M. Dzhemilev
DOI:10.1016/j.tet.2018.07.031
日期:2018.8
An original strategy has been developed for the synthesis of valuable unsaturated macrocyclic lactones, macrodiolides, containing a 1Z,5Z-diene moiety in 57–79% yields and >98% stereoselectivity by hafnium triflate Hf(OTf)4-catalyzed intermolecular esterification of aliphatic α,ω-dicarboxylic acids with α,ω-alka-nZ,(n+4)Z-dienediols (1,12-dodeca-4Z,8Z-dienediol, 1,14-tetradeca-5Z,9Z-dienediol, 1,18-octadeca-7Z
已开发出一种用于合成有价值的不饱和大环内酯,大环内酯的原始策略,该化合物通过三氟甲磺酸H Hf(OTf)4催化的脂肪族分子间酯化反应以57-79%的收率和> 98%的立体选择性包含1Z,5Z-二烯部分。α,ω-二羧酸与α,ω-烷基-nZ,(n + 4)Z-二烯二醇(1,12-dodeca-4Z,8Z-二烯二醇,1,14-十四碳-5Z,9Z-二烯二醇,1, 18-十八烷基-7Z,11Z-二烯二醇)。二醇是通过在Mg金属和Cp 2 TiCl 2催化剂(10摩尔%)存在下,将含氧1,2-二烯的四氢吡喃醚与EtMgBr进行均相环化而得到的。所得的大环糖苷在体外对Jurkat,K562,U937,Hek293和HeLa肿瘤细胞系表现出高细胞毒活性。