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Studies on the Synthesis of Orthogonally Protected Azalanthionines, and of Routes towards b-Methyl Azalanthionines, by Ring-Opening of N-Activated Aziridine-2-Crboxylates
O'Brien, Keith; Ó Proinsias, Keith; Kelleher, Fintan
Orthogonally protected azalanthionines were successfully synthesised by the ring-opening of N-activated aziridine-2-carboxylates with protected diaminopropanoic acids (DAPs). The required DAPs were also prepared by ring-opening of N-activated aziridine-2-carboxylates with para-methoxybenzylamine, but it was found that the choice of aziridine protecting groups dictated both the success of the reaction as well as the regioselectivity of the isolated products. Attempts to extend the methodology to the preparation of the more sterically demanding b-methyl azalanthionines have, so far, been unsuccessful.
Keyword(s): 1; 2-Diaminopropanoic acids (DAPs); Lanthionine; Aziridine; Aziridine-2-carboxylates; Ring-opening; Azalanthionines; b-Methyl azalanthionines; Medicinal-Pharmaceutical Chemistry; Organic Chemistry
Publication Date:
2014
Type: Other
Peer-Reviewed: Unknown
Contributor(s): Higher Education Authority; Programme for Research in Third-Level Institutions IV
Institution: Dublin Institute of Technology
Citation(s): Articles
Publisher(s): Dublin Institute of Technology
File Format(s): application/pdf
First Indexed: 2014-07-17 05:58:34 Last Updated: 2017-12-14 06:57:23