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Four‐Component Assembly of Natural‐Product‐Like Ring‐Fused Isoquinuclidines
Author(s) -
Sellstedt Magnus,
Dang Hung The,
Prasad G. Krishna,
Sauer Uwe,
Almqvist Fredrik
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301371
Subject(s) - chemistry , natural product , ring (chemistry) , intramolecular force , diastereomer , component (thermodynamics) , carbon fibers , stereochemistry , organic chemistry , physics , materials science , composite number , composite material , thermodynamics
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.