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New Members of the Cinchona Alkaloid Family: 9‐Aminoquincorine‐10‐aldehyde and 9‐Aminoquincoridine‐10‐aldehyde
Author(s) -
Neda Ion,
Fodor Elena,
Maftei Catalin V.,
Mihorianu Monica,
Ambrosi HorstDieter,
Franz M. Heiko
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.201301286
Subject(s) - aldehyde , chemistry , enantiopure drug , moiety , cinchona , alkaloid , cinchona alkaloids , organic chemistry , enantioselective synthesis , stereochemistry , combinatorial chemistry , catalysis
This paper reports the synthesis of the new enantiopure amino aldehydes, 9‐aminoquincorine‐10‐aldehyde ( 1 ) and 9‐aminoquincoridine‐10‐aldehyde ( 2 ). These alkaloid‐like compounds are derivatives of the Cinchona alkaloids quinine and quinidine. Their application as chiral building blocks in the synthesis of novel compounds is demonstrated by the reduction and reductive amidation of the aldehyde moiety. Furthermore, their use in early drug discovery and supramolecular chemistry is described.