桦木醇为起始原料经关键氧化构建 HIV 成熟抑制剂 BMS-955176。
Synthesis of HIV-Maturation Inhibitor BMS-955176 from Betulin by an Enabling Oxidation Strategy.
机构信息
Chemical and Synthetic Development, Bristol-Myers Squibb , 1 Squibb Drive, New Brunswick, New Jersey 08903, United States.
出版信息
J Org Chem. 2017 May 5;82(9):4958-4963. doi: 10.1021/acs.joc.7b00438. Epub 2017 Apr 19.
A concise and scalable second generation synthesis of HIV maturation inhibitor BMS-955176 is described. The synthesis is framed by an oxidation strategy highlighted by a Cu mediated aerobic oxidation of betulin, a highly selective PIFA mediated dehydrogenation of an oxime, and a subsequent Lossen rearrangement which occurs through a unique reaction mechanism for the installation of the C17 amino functionality. The synthetic route proceeds in 7 steps with 47% overall yield and begins from the abundant and inexpensive natural product betulin.
本文描述了一种简洁且可扩展的第二代 HIV 成熟抑制剂 BMS-955176 的合成方法。该合成方法以氧化策略为框架，其中包括一种 Cu 介导的桦木醇有氧氧化、一种高度选择性的 PIFA 介导的肟脱氢以及随后的 Lossen 重排，该重排通过独特的反应机制进行，用于安装 C17 氨基官能团。该合成路线经过 7 步反应，总收率为 47%，起始原料为丰富且廉价的天然产物桦木醇。
Zotero 插件