Synthesis of 1-amino-3-[(dihydroxyboryl)methyl]-cyclobutanecarboxylic acid as a potential therapy agent

George Kabalka, Min Liang Yao

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

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.

Original languageEnglish (US)
Pages (from-to)8280-8286
Number of pages7
JournalJournal of Organic Chemistry
Volume69
Issue number24
DOIs
StatePublished - Nov 26 2004

Fingerprint

Cyclic Amino Acids
Hydantoins
Boron
Neutrons
1-aminocyclobutanecarboxylic acid
1-amino-3-((dihydroxyboryl)methyl)- cyclobutanecarboxylic acid

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Synthesis of 1-amino-3-[(dihydroxyboryl)methyl]-cyclobutanecarboxylic acid as a potential therapy agent. / Kabalka, George; Yao, Min Liang.

In: Journal of Organic Chemistry, Vol. 69, No. 24, 26.11.2004, p. 8280-8286.

Research output: Contribution to journalArticle

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