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Review | Regular issue | Vol 92, No. 1, 2016, pp.31-43
Published online, 17th December, 2015
DOI: 10.3987/REV-15-829
■ Applications of C-H Insertion Reaction in Total Synthesis of Biologically Active Heterocyclic Natural Products

Toshiyuki Kan,* Tomohiro Asakawa, and Makoto Inai

*Synthetic Organic ＆ Medicinal Chemistry, School of Pharmaceutical Science, University of Shizuoka, 52-1 Yada, Suruga, Shizuoka 422-8526, Japan

Abstract

Here, we summarize our work on applications of the Rh-catalyzed C-H insertion reaction to syntheses of heterocyclic natural products. Total synthesis of racemic serotobenine (4) was achieved in an optical active form. Enantioselective synthesis of SB-203207 (25) was accomplished via desymmetric C-H insertion reaction of 33 to construct the bicyclo[3.3.0] framework. Stereoselective synthesis of MFPA (53) was accomplished with the aid of an intermolecular C-H insertion reaction. Synthesis of aperidine (70) featured cis-selective construction of the dihydrobenzofuran ring of 81 by utilizing Hashimoto’s catalyst.