A tandem Diels-Alder/Mannich approach to the synthesis of AE and ABE ring analogues of Delphinium alkaloids

被引：19
作者：
Goodall, Kirsten J. [1 ]
Brimble, Margaret A. [1 ]
Barker, David [1 ]
机构：
[1] Univ Auckland, Sch Chem Sci, Auckland 1, New Zealand
来源：
TETRAHEDRON | 2012年 / 68卷 / 29期
关键词：
Delphinium alkaloids; azabicyclo[3.3.1]nonanes; Mannich reaction; Diels-Alder reaction; IMINIUM ION CYCLIZATIONS; STEREOSELECTIVE-SYNTHESIS; PIPERIDINE ALKALOIDS; EFFICIENT SYNTHESIS; METHYLLYCACONITINE; ANTAGONIST; INHIBITORS; RAT;
D O I：
10.1016/j.tet.2012.05.037
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The one-pot TiCl4 catalysed Diels-Alder/Mannich reaction of alpha-cyanoaminoacrylates with 2-silyloxy-1,4-butadienes gives 6-keto-3-azabicyclo[3.3.1]nonane-1-carboxylates. Reduction of the ketone and alkylation of the resultant alcohol gives 6-alkoxy-3-azabicyclo[3.3.1]nonanes mimicking the AE rings of a number of Delphinium and Aconitum alkaloids, with the same stereochemistry as the natural products. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5759 / 5778
页数：20
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