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

页码：8629 / 8632

页数：4