Sun Xue, Liu Yi, Liu Jun, Gu Guofeng, Du Yuguo
State Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China.
Org Biomol Chem. 2015 Apr 14;13(14):4271-7. doi: 10.1039/c5ob00093a. Epub 2015 Mar 11.
A concise total synthesis of the natural product bacillamide B was accomplished in 30% overall yield starting from L-cystine. The key step was a one-pot four-step process of thiazoline formation via a cascade disulfide cleavage/thiocarbonylation/Staudinger reduction/aza-Wittig reaction using β-azido disulfide and carboxylic acid as substrates. The absolute configuration of the natural bacillamide B was reconfirmed to be S and the specific optical rotation was revised to (-).
以L-胱氨酸为起始原料，以30%的总收率完成了天然产物杆菌酰胺B的简洁全合成。关键步骤是一锅法四步反应，以β-叠氮二硫化物和羧酸为底物，通过级联二硫键裂解/硫羰基化/施陶丁格还原/氮杂维蒂希反应形成噻唑啉。重新确认天然杆菌酰胺B的绝对构型为S型，比旋光度修正为（-）。
