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Concise and Diversity‐Oriented Route toward Polysubstituted 2‐Aminoimidazole Alkaloids and Their Analogues
Author(s) -
Ermolat'ev Denis S.,
Bariwal Jitender B.,
Steenackers Hans P. L.,
De Keersmaecker Sigrid C. J.,
Van der Eycken Erik V.
Publication year - 2010
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201004256
Subject(s) - carbodiimide , intramolecular force , chemistry , combinatorial chemistry , core (optical fiber) , stereochemistry , organic chemistry , computer science , telecommunications
Alkaloids of the naamine family were synthesized from diverse propargylamines in just two steps (see scheme: R 1 =Me, R 2 =substituted benzyl, R 3 =Ar). Thus, the addition to a propargylamine of a carbodiimide generated in situ, silver(I)‐catalyzed intramolecular hydroamidation, and subsquent deprotection provide access to the heterocyclic core of numerous natural products and biologically active compounds. Boc= tert ‐butoxycarbonyl, Cbz=carbobenzyloxy.