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Copper‐Catalyzed Synthesis of a Highly Hydroxy‐Functionalized Benzo[ e ]indolizidine by Intramolecular N ‐Arylation
Author(s) -
Cordero Franca M.,
Khairnar Bhushan B.,
Bonanno Paola,
Martinelli Andrea,
Brandi Alberto
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.201300440
Subject(s) - chemistry , indolizidine , enantiopure drug , intramolecular force , pyrrolidine , catalysis , cycloaddition , quinoline , stereochemistry , medicinal chemistry , 1,3 dipolar cycloaddition , combinatorial chemistry , enantioselective synthesis , organic chemistry , alkaloid
The enantiopure (2 S ,3 S ,3a S ,5 S )‐1,2,3,3a,4,5‐hexahydropyrrolo[1,2‐ a ]quinoline‐2,3,5‐triol (2,3,5‐trihydroxybenzo[ e ]indolizidine) framework has been synthesized by a straightforward strategy consisting of 1,3‐dipolar cycloaddition of a pyrroline N ‐oxide to 2‐bromostyrene followed by isoxazolidine N–O bond reduction and cyclization by copper‐catalyzed nucleophilic aromatic substitution of the intermediate pyrrolidine.