HETEROCYCLES

Paper | Regular issue | Vol. 91, No. 3, 2015, pp. 573-582
Received, 26th December, 2014, Accepted, 20th January, 2015, Published online, 30th January, 2015.
DOI: 10.3987/COM-14-13163

■ Syntheses of a Pyrrolidine Analog of a Tetrahydrofuran Containing Acetogenin, cis-Solamin

Kouji Ohnishi, Haruka Sakurai, Kazuya Kobayashi, Hidefumi Makabe, Kenta Teruya, Kenichi Akaji, and Yasunao Hattori*

Department of Medicinal Chemistry, Pharmacetuical Chemistry, Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan

Abstract

Practical synthesis of a pyrrolidine analog of a mono-THF acetogenin as a proto-type analog to evaluate the effect of a heteroatom in the mono-THF ring of acetogenins was achieved using Pd(II)-catalyzed diastereo-selective cyclization. Ligand-less PdCl2 catalyzed cyclization yielded the desired pyrrolidine derivative as a single major product having the desired relative configurations. Coupling of the pyrrolidine fragment with a known γ-lactone-containing fragment via a Sonogashira cross-coupling reaction yielded the desired aza-cis-solamin analog.

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