Asymmetric Total Synthesis of Ieodomycin B.
Asymmetric Total Synthesis of Ieodomycin B.
复制标题
碘霉素B的不对称全合成
DOI：
10.3390/md15010017
复制
发表时间：
2017-01-18
期刊：
影响因子：
5.4
通讯作者：
Wang X
中科院分区：
文献类型：
--
作者：
Lin S;Zhang J;Zhang Z;Xu T;Huang S;Wang X
从一株海洋芽孢杆菌中分离得到具有体外抗菌活性的Ieomycin B。以市售香叶醇为原料，实现了一种新的不对称全合成依多霉素B的方法。该方法包括通过Crimmins修饰的Evans Aldol反应和对甲氧基苄基保护的醛的螯合控制的Mukaiyama Aldol反应在C-3和C-5位生成1，3-反式二羟基，以及在去保护-内酯化一锅反应中生成内酯环。
Ieodomycin B, which shows in vitro antimicrobial activity, was isolated from a marine Bacillus species. A novel asymmetric total synthetic approach to ieodomycin B using commercially available geraniol was achieved. The approach involves the generation of 1,3-trans-dihydroxyl at C-3 and C-5 positions via a Crimmins-modified Evans aldol reaction and a chelation-controlled Mukaiyama aldol reaction of a p-methoxybenzyl-protected aldehyde, as well as the generation of a lactone ring in a deprotection–lactonization one-pot reaction.