使用有机催化剂对拉坦前列素进行对映选择性和非对映选择性合成。
Enantio- and Diastereoselective Synthesis of Latanoprost using an Organocatalyst.
机构信息
Department of Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai, 980-8578, Japan.
Faculty of Advanced Life Science, Frontier Research Center for, Advanced Material and Life Science, Hokkaido University, Kita 21 Nishi 11, Sapporo, 001-0021, Japan.
出版信息
Chemistry. 2018 Jun 12;24(33):8409-8414. doi: 10.1002/chem.201800829. Epub 2018 May 22.
An enantioselective total synthesis of latanoprost was achieved. Its chiral cyclopentane core structure was constructed through an organocatalyst-mediated [3+2]-cycloaddition reaction, and chirality in the ω-side chain was generated by prolinate-anion-mediated α-aminoxylation of an aldehyde. Highly diastereoselective domino acetalization and an oxy-Michael reaction were key steps for the generation of C9 chirality.
实现了拉坦前列素的对映选择性全合成。其手性环戊烷核心结构通过有机催化剂介导的[3+2]-环加成反应构建，ω-侧链的手性通过脯氨酸-阴离子介导的醛的α-氨氧化反应产生。高度非对映选择性的多步缩醛化和氧迈克尔加成反应是生成 C9 手性的关键步骤。
Zotero 插件