Concise and Diversity‐Oriented Route toward Polysubstituted 2‐Aminoimidazole Alkaloids and Their Analogues | Zendy

Ermolat'ev Denis S. | Zendy; Bariwal Jitender B. | Zendy; Steenackers Hans P. L. | Zendy; De Keersmaecker Sigrid C. J. | Zendy; Van der Eycken Erik V. | Zendy

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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.

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