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A novel samarium(II)-mediated tandem spirocyclization onto an aromatic ring |
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| Authors: | Hiroki IwasakiNozomi Tsutsui Toru EguchiHiroaki Ohno Masayuki Yamashita Tetsuaki Tanaka |
| Institution: | a Department of Pharmaceutical Manufacturing Chemistry, Kyoto Pharmaceutical University, 1 Misasagi-Shichono-cho, Yamashina-ku, Kyoto 607-8412, Japan b Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan |
| Abstract: | We report a samarium(II)-mediated tandem spirocyclization reaction to provide dispiro4.2.4.2]tetradecadiene and dispiro4.2.5.2]pentadecadiene skeletons. The reaction was achieved by intramolecular addition of a ketyl radical onto an aromatic ring bearing an electrophilic moiety followed by reductive capture of the spirohexadienyl radical intermediate with SmI2 in the presence of HMPA. |
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