Scalable total synthesis of a mycobactin T analogue utilizing a novel synthetic and protection strategy
Scalable total synthesis of a mycobactin T analogue utilizing a novel synthetic and protection strategy
复制标题
利用新型合成和保护策略可大规模全合成分枝杆菌素 T 类似物
DOI：
10.1039/c9qo00502a
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发表时间：
2019
影响因子：
5.4
通讯作者：
Liu Gang
中科院分区：
文献类型：
--
作者：
Wu Jie;Mu Ran;Liu Zi Jie;Lu Shi Chao;Liu Gang
分枝杆菌素T类似物1（MbT-1）是一种分枝杆菌特异性铁载体类似物，通常用于偶联治疗药物以诱导选择性抗菌活性。本论文以16步反应完成了MbT-1的全合成，总收率为14%。对常见中间体7和反应条件的明智选择允许两个主要结构单元B和D的简明合成。关键步骤包括一锅法合成手性结构单元保护的A，一种新的保护策略（O-Bz/t-BuCO 2/Cbz）和一种选择性脱保护方法（O-Bz/Boc/Cbz），该方法可用于其他分枝杆菌素类似物的合成。
Mycobactin T analogue 1 (MbT-1) is a mycobacterial-specific siderophore analogue, which is usually employed to conjugate therapeutic drugs to induce selective antibacterial activity. In this article, the scalable total synthesis of MbT-1 was accomplished with a 16-step procedure in a total yield of 14%. A judicious choice of common intermediate 7 and reaction conditions allowed for the concise synthesis of two major building blocks B and D. Key steps included one-pot synthesis of chiral building block protected A, a novel protection strategy (O-Bz/t-BuCO2/Cbz), and a selective deprotection method (O-Bz/Boc/Cbz), which could help in the syntheses of other mycobactin analogues.