Tetrahedron

Synthesis of (3′ R, 5′ S)-3′-hydroxycotinine using 1, 3-dipolar cycloaddition of a nitrone

O Tamura, A Kanoh, M Yamashita, H Ishibashi

文献索引：Tamura, Osamu; Kanoh, Ayano; Yamashita, Masayuki; Ishibashi, Hiroyuki Tetrahedron, 2004 , vol. 60, # 44 p. 9997 - 10003

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被引用次数: 29

摘要

To synthesize (3′ R, 5′ S)-3′-hydroxycotinine [], the main metabolite of nicotine (), cycloaddition of C-(3-pyridyl) nitrones,, and with (2R)-and (2S)-N-(acryloyl) bornane-10, 2- sultam [(2R)-and] was examined. Among them, l-gulose-derived nitrone underwent stereoselective cycloaddition with to afford cycloadduct, which was elaborated to.