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

被引：30
|
作者：
Tamura, O [1 ]
Kanoh, A
Yamashita, M
Ishibashi, H
机构：
[1] Kanazawa Univ, Grad Sch Nat Sci & Technol, Div Pharmaceut Sci, Kanazawa, Ishikawa 9201192, Japan
[2] Kyoto Pharmaceut Univ, Kyoto 6078414, Japan
来源：
TETRAHEDRON | 2004年 / 60卷 / 44期
关键词：
(3; R; 5; S)-3-hydroxycotinine; L-gulose-derived nitrone; cycloaddition;
D O I：
10.1016/j.tet.2004.08.023
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
To synthesize (3'R,5'S)-3'-hydroxycotinine [(+)-1], the main metabolite of nicotine (2), cycloaddition of C-(3-pyridyl)nitrones 3a, 3c, and 15 with (2R)- and (2S)-N-(acryloyl)bomane-10,2-sultam [(2R)- and (2S)-8] was examined. Among them, L-gulose-derived nitrone 15 underwent stercoselective cycloaddition with (2S)-8 to afford cycloadduct 16, which was elaborated to (+)-1. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码：9997 / 10003
页数：7
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