Synthesis of 1-amino-3-[(dihydroxyboryl)methyl]- cyclobutanecarboxylic acid as a potential therapy agent.
A novel boronated aminocyclobutanecarboxylic acid (1) was synthesized for potential use in boron neutron capture therapy. Starting from the readily available 3-(bromomethyl)cyclobutanone ketal (4), several synthetic routes to 1 were evaluated. After several unsuccessful attempts with traditional synthetic methods, a novel synthetic strategy to generate the new boronated cyclic amino acid was developed. The tolerance of the hydantoin group to the selenoxide elimination reaction conditions in the preparation of alkenyl compound 7 proved to be the key step in the new strategy.
Kabalka
George W
GW
Department of Chemistry, The University of Tennessee, Knoxville, Tennessee 37996-1600, USA. kabalka@utk.edu
Yao
Min-Liang
ML
D001895:Boron / Q000737:chemistry; D016754:Boron Neutron Capture Therapy; D002264:Carboxylic Acids / Q000138:chemical synthesis*; D003503:Cyclobutanes / Q000138:chemical synthesis*; D006801:Humans; D008968:Molecular Conformation; D011838:Radiation-Sensitizing Agents / Q000138:chemical synthesis*
C494949:1-amino-3-((dihydroxyboryl)methyl)- cyclobutanecarboxylic acid; D002264:Carboxylic Acids; D003503:Cyclobutanes; D011838:Radiation-Sensitizing Agents; D001895:Boron