Enantioselective total synthesis of aperidine |
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Authors: | Wakimoto Toshiyuki Miyata Kakeru Ohuchi Hitoshi Asakawa Tomohiro Nukaya Haruo Suwa Yoshihide Kan Toshiyuki |
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Institution: | School of Pharmaceutical Sciences, University of Shizuoka and Global COE Program, Suruga-ku, Shizuoka, Japan. wakimoto@mol.f.u-tokyo.ac.jp |
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Abstract: | An efficient total synthesis of aperidine was accomplished using a Rh-catalyzed C-H insertion of a cis-dihydrobenzofuran ring. To circumvent the facile epimerization of the cis-dihydrobenzofuran ring, we designed and prepared the C-H insertion precursor diazoamide by Raines' protocol. Finally, the efficient incorporation of a guanidine group and mild deprotection conditions yielded this labile natural product. |
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