1,5-Translocation Strategy for Nucleoside Anomeric Radicals

Atsushi Kittaka School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo, 142, Japan

Hiromichi Tanaka School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo, 142, Japan

Naoki Yamada School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo, 142, Japan

Hajime Kato School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo, 142, Japan

Tadashi Miyasaka School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo, 142, Japan

Abstract

A new method for generating nucleoside anomeric radicals utilizing radical 1,5-translocation was developed. Two kinds of β-halogenovinyl groups at the C6-position of uracil nucleosides were found to be a good radical source, which subsequently forms a nucleoside anomeric radical. The following 5-endo-trig cyclization gave anomeric spiro nucleosides as products.

Notes

Some of these compounds were also isolated by the HPLC separation in 24% combined yield (data not shown)

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1,5-Translocation Strategy for Nucleoside Anomeric Radicals

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1,5-Translocation Strategy for Nucleoside Anomeric Radicals

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