Scalable Total Synthesis of Leucascandrolide A Macrolactone Using a Chiral Phosphoric Acid/CuX Combined Catalytic System
Scalable Total Synthesis of Leucascandrolide A Macrolactone Using a Chiral Phosphoric Acid/CuX Combined Catalytic System
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DOI：
10.1021/acs.orglett.3c00450
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发表时间：
2023-03-15
期刊：
影响因子：
5.2
通讯作者：
Terada，Masahiro
中科院分区：
文献类型：
--
作者：
Umemiya，Shigenobu;Shinagawa，Naoya;Terada，Masahiro
利用现成的原料，通过最长的 17 个步骤的线性序列完成了 leucascandrolide A 大环内酯的可扩展全合成，产率为 31.2%。该合成的关键步骤是手性磷酸（CPA）/CuBr协同催化下的对映选择性烯丙基化反应以及CPA与CuCl存在下的非对映选择性催化巴豆酰化反应。这些催化反应可以在克级进行，以提供具有优异立体选择性的所需产物。
A scalable total synthesis of leucascandrolide A macrolactone has been accomplished with a longest linear sequence of 17 steps from readily available feedstocks in 31.2% yield. The key steps in this synthesis are the enantioselective allylation reaction by chiral phosphoric acid (CPA)/CuBr cooperative catalysis and the diastereoselective catalytic crotylation in the presence of CPA with CuCl. These catalytic reactions can be performed on a gram scale to afford the desired products with excellent stereoselectivities.