Flow synthesis of tricyclic spiropiperidines as building blocks for the histrionicotoxin family of alkaloids

被引：40

作者：

Brasholz, Malte ^{[1
]}

Johnson, Brian A. ^{[2
]}

Macdonald, James M. ^{[1
]}

Polyzos, Anastasios ^{[1
]}

Tsanaktsidis, John ^{[1
]}

Saubern, Simon ^{[1
]}

Holmes, Andrew B. ^{[1
,2
]}

Ryan, John H. ^{[1
]}

机构：

[1] CSIRO Mol & Hlth Technol, Clayton, Vic 3168, Australia

[2] Univ Melbourne, Sch Chem, Bio Inst 21, Parkville, Vic 3010, Australia

来源：

TETRAHEDRON | 2010年 / 66卷 / 33期

基金：

澳大利亚研究理事会;

关键词：

Flow chemistry; Domino reactions; Spiropiperidines; Olefination reactions; 1,3-Dipolar cycloaddition; ORGANIC-SYNTHESIS; 2-DIRECTIONAL SYNTHESIS; MULTISTEP SYNTHESIS; (-)-HISTRIONICOTOXIN; CHEMISTRY; REACTORS;

D O I：

10.1016/j.tet.2010.04.092

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A domino cyclization reaction of the bis-unsaturated ketone 3 with hydroxylamine proceeds with good yield and high stereoselectivity, in a flow reactor system. The tricyclic spiropiperidine products 5 and 2 obtained are valuable building blocks for the synthesis of analogues of the histrionicotoxin alkaloids. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：6445 / 6449

页数：5

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