赫替霉素A-F的不对称全合成

Wu Gang, Wang Ting, Jiang Zhongke, Liu Shaowei, Sun Chenghang

Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China.

ACS Omega. 2021 Mar 17;6(12):8239-8245. doi: 10.1021/acsomega.0c06267. eCollection 2021 Mar 30.

Herein, we report a concise and stereoselective approach for the asymmetric total synthesis of hetiamacins A-F on the basis of the total synthesis of amicoumacin C, which could be synthesized from a known l-aspartic acid derivative. The synthesis of hetiamacin A was accomplished by an 11-step sequence that featured 1,3-oxazinane ring formation of amicoumacin B followed by amidation in one pot. Hetiamacins B-F were synthesized from amicoumacin A in only one step.

在此，我们报道了一种基于氨甲香豆霉素C的全合成，对赫替马菌素A - F进行不对称全合成的简洁且立体选择性的方法，氨甲香豆霉素C可由一种已知的L - 天冬氨酸衍生物合成。赫替马菌素A的合成通过一个11步的序列完成，其特点是氨甲香豆霉素B形成1,3 - 恶嗪烷环，然后一锅法进行酰胺化反应。赫替马菌素B - F仅通过一步反应由氨甲香豆霉素A合成。