Please use this identifier to cite or link to this item: https://scidar.kg.ac.rs/handle/123456789/9088
Title: Synthesis of Angularly Fused (Homo)triquinane-Type Hydantoins as Precursors of Bicyclic Prolines
Authors: Šmit, Biljana
Rodic, Marko
Pavlovic, Radisa
Journal: Synthesis (Germany)
Issue Date: 2-Feb-2016
Abstract: © Georg Thieme Verlag Stuttgart · New York-Synthesis 2016. An efficient strategy for a four-step synthesis of angularly fused tricyclic hydantoins as suitable precursors of cis-fused bicyclic α-amino acids is developed by combining a highly diastereoselective Bucherer-Bergs reaction of 2-alkenylcycloalkanones and a regiospecific selenium-induced closure of pyrrolidine ring. This methodology was applied in a five-step synthesis of bicycloproline derivatives in high overall yield. The method could be used for the multigram preparation of free conformationally constrained bicyclic α-amino acids with two points of diversity (size of cycloalkyl ring and substituent at the pyrrolidine ring).
URI: https://scidar.kg.ac.rs/handle/123456789/9088
Type: article
DOI: 10.1055/s-0035-1561285
ISSN: 00397881
SCOPUS: 84955188563
Appears in Collections:Institute for Information Technologies, Kragujevac

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