Enantioselective total synthesis of (2R,3R,6R)-N-methyl-6-(deca-1′,3′,5′-trienyl)-3-methoxy-2-methylpiperidine, an insecticidal alkaloid

被引：15
|
作者：
Nakatani, Y [1 ]
Oshita, J [1 ]
Ishigami, K [1 ]
Watanabe, H [1 ]
Kitahara, T [1 ]
机构：
[1] Univ Tokyo, Grad Sch Agr & Life Sci, Dept Appl Biol Chem, Bunkyo Ku, Tokyo 1138657, Japan
来源：
TETRAHEDRON | 2006年 / 62卷 / 01期
关键词：
enantioselective; alkaloid; piperidine ring;
D O I：
10.1016/j.tet.2005.09.121
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An insecticidal piperidine alkaloid, (2R,3R,6R)-N-methyl-6-(deca-1',3',5-trienyl)-3-methoxy-2-methylpiperidine, was efficiently synthesized in a stereoselective manner starting from D-alanine. Chiral center at C-6 was controlled by hydrogenation of imine and side chain was introduced by Julia olefination. The absolute configuration of natural product was determined to be 2R, 3R, 6R. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：160 / 165
页数：6
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