Department of Synthetic Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Hoshi University , 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan.
Org Lett. 2018 Feb 16;20(4):1031-1033. doi: 10.1021/acs.orglett.7b03979. Epub 2018 Jan 23.
In this work, the protecting-group-free total synthesis and stereochemical assignment of (-)-boscartin F have been reported. The key steps, including Sharpless asymmetric epoxidation, I-mediated iodoetherification, aldol reaction, and ring-closing metathesis, allowed for rapid and highly stereoselective access to boscartin F. In addition, single-crystal X-ray crystallographic analysis of the semicarbazone derivative 22 confirmed the stereochemistry of boscartin F.
本文报道了（-）-波沙他汀 F 的无保护基全合成和立体化学构型确定。关键步骤包括：Sharpless 不对称环氧化、碘介导的碘醚化、羟醛缩合反应和闭环复分解反应，这些步骤能够快速、高立体选择性地得到波沙他汀 F。此外，通过对半卡巴腙衍生物 22 的单晶 X 射线晶体学分析，确定了波沙他汀 F 的立体化学构型。
