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Enantioselective, Protecting-Group-Free Total Synthesis of Boscartin F. 2018
Department of Synthetic Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Hoshi University , 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan.
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, I2-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.
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