Four-Component Assembly of Natural-Product-Like Ring-Fused Isoquinuclidines

A four‐component reaction between formyl‐substituted 2‐pyridones, aldehydes, amines, and activated alkenes has been developed. The resulting products are ring‐fused natural‐product‐like isoquinuclidines. Three carbon–carbon bonds, two carbon–nitrogen bonds, and four or five stereocentres are formed...

Full description

Saved in:
Bibliographic Details
Published in:European journal of organic chemistry 2013-11, Vol.2013 (33), p.7476-7479
Main Authors: Sellstedt, Magnus, Dang, Hung The, Prasad, G. Krishna, Sauer, Uwe, Almqvist, Fredrik
Format: Article
Language:English
Subjects:
Carbon
Fused-ring systems
Multicomponent reactions
Natural products
Nitrogen­ heterocycles
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A four‐component reaction between formyl‐substituted 2‐pyridones, aldehydes, amines, and activated alkenes has been developed. The resulting products are ring‐fused natural‐product‐like isoquinuclidines. Three carbon–carbon bonds, two carbon–nitrogen bonds, and four or five stereocentres are formed in the reaction with overall product yields in the range 23–67 %. In most cases a single diastereomer was obtained. An intramolecular version of the reaction yielded analogues of the multi‐ring‐fused natural product catharanthine in a single step. A four‐component reaction that generates natural‐product‐like ring‐fused isoquinuclidines has been developed. Three carbon–carbon bonds, two carbon–nitrogen bonds, and four or five stereocentres are formed in the reaction and an intramolecular version of the reaction yields analogues of the natural product catharanthine in a single step.
ISSN:1434-193X
1099-0690
1099-0690
DOI:10.1002/ejoc.201301371