Department of Applied Chemistry, Faculty of Engineering, Osaka Institute of Technology , 5-16-1 Ohmiya, Asahi-ku, Osaka 535-8585, Japan.
J Org Chem. 2018 Feb 2;83(3):1606-1613. doi: 10.1021/acs.joc.7b02916. Epub 2018 Jan 12.
We report short syntheses of (-)-tripterifordin and (-)-neotripterifordin, potent inhibitors of HIV replication, from stevioside, a natural sweetener used worldwide. The key transformations are reduction at C13 through the formation of a tertiary chloride and subsequent three-step lactonization including a selective iodination at C20 by the photoreaction of the C19-alcohol. The title compounds were reliably obtained from stevioside in 9 and 11 steps (with 5-7 isolation steps), respectively. Additionally, the related lactone-containing ent-kaurenes, doianoterpenes A and B, and two more natural products were synthesized.
我们报告了 (-)- 三萜佛丁和 (-)- 新三萜佛丁的短合成，它们是抑制 HIV 复制的有效抑制剂，来源于甜菊糖，这是一种在全球范围内使用的天然甜味剂。关键的转化是通过形成叔氯和随后的三步内酯化在 C13 处还原，包括通过 C19-醇的光反应在 C20 处选择性碘化。这两个标题化合物分别从甜菊糖中以 9 步和 11 步（带有 5-7 步分离步骤）可靠地获得。此外，还合成了相关的含内酯的贝壳杉烯、多异贝壳杉烯 A 和 B 以及另外两种天然产物。
