Application of an organozinc reagent derived from (S)-pyroglutamic acid:: a formal synthesis of epibatidine

被引：28
|
作者：
Karstens, WFJ [1 ]
Moolenaar, MJ [1 ]
Rutjes, FPJT [1 ]
Grabowska, U [1 ]
Speckamp, WN [1 ]
Hiemstra, H [1 ]
机构：
[1] Univ Amsterdam, Inst Mol Chem, Organ Chem Lab, NL-1018 WS Amsterdam, Netherlands
来源：
TETRAHEDRON LETTERS | 1999年 / 40卷 / 49期
关键词：
epibatidine; organozinc reagent; N-acyliminium ions; azabicylo[2.2.1]heptanes;
D O I：
10.1016/S0040-4039(99)01808-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A formal total synthesis of natural (-)-epibatidine has been developed. Key steps in the synthesis are a copper(I)-mediated coupling of an (S)-pyroglutamic acid-derived organozine reagent with 1-iodo-3-trimethylsilyl-1-propyne and an N-acyl- or N-sulfonyliminium ion cyclization, Following this route, various N-protected hydroxylactams were converted into 7-azabicylo[2,2,1]heptane derivatives, (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：8629 / 8632
页数：4
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