Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan.
Org Lett. 2023 Mar 24;25(11):1924-1928. doi: 10.1021/acs.orglett.3c00450. Epub 2023 Mar 15.
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.
已实现从易得原料经 17 步线性反应以 31.2%总收率规模化全合成 Leucascandrolide A 大环内酯，其中关键步骤包括手性磷酸（CPA）/CuBr 协同催化的对映选择性烯丙基化反应，以及在 CPA 和 CuCl 存在下的非对映选择性催化羟丙基化反应。这些催化反应可在克级规模下进行，以优异的立体选择性得到目标产物。
