Synthesis 2018; 50(07): 1546-1554
DOI: 10.1055/s-0036-1589148
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Novel Oxazolyl Amino Acids and Their Use in the Parallel Synthesis of Disubstituted Oxazole Libraries

Siva Murru
a  University of Louisiana Monroe, 700 University Avenue, Monroe, Louisiana, 71209, USA   Email: murru@ulm.edu
,
Ramesh Bista
a  University of Louisiana Monroe, 700 University Avenue, Monroe, Louisiana, 71209, USA   Email: murru@ulm.edu
,
Adel Nefzi*
b  Torrey Pines Institute for Molecular Studies, 11350 SW Village Parkway, Port St Lucie, Florida 34987, USA   Email: adeln@tpims.org
› Author Affiliations
The authors would like to thank the State of Florida Funding, NIH (1R21CA191351-01A1 Nefzi/Piedrafita), NIH (1R01AI105836-01A1, Nefzi/Piedrafita), and Louisiana Biomedical Research Network (Murru) for providing generous financial support.
Further Information

Publication History

Received: 06 November 2017

Accepted after revision: 14 November 2017

Publication Date:
19 January 2018 (online)


Abstract

Novel chiral oxazolyl alanine and homologues are synthesized and utilized as building blocks for the solid-phase parallel synthesis of novel trifunctional oxazole small molecules in good to excellent overall yields and with high purity. The orthogonal deprotection strategy of oxazolyl amino acids, prepared from serine methyl ester and amino acids such as aspartic and glutamic acids, allows multiple sites of diversification to make a variety of pharmacologically relevant small molecules. The general nature of this approach allows the preparation of a large number of small molecules and peptidomimetics.

Supporting Information

 
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