Synthesis of 1-Amino-3-[2-(1,7-dicarba-closo-dodecaboran(12)-1-yl)ethyl]cyclobutanecarboxylic Acid: A Potential BNCT Agent.
The synthesis of an unnatural amino acid, 1-amino-3-[2-(1,7-dicarba-closo-dodecaboran(12)-1-yl)ethyl]cyclobutanecarboxylic acid, was achieved. This new potential BNCT agent was prepared via the monoalkylation of m-carborane with 4-bromobutene to produce 4-m-carboranyl-1-butene, which was then subjected to a 2 + 2 cycloaddition using dichloroketene. The resultant boronated cyclobutanone was reductively dechlorinated prior to the formation of the corresponding hydantoin, which was hydrolized to the title compound in excellent yield.
Srivastava
Rajiv R.
RR
Departments of Chemistry and Radiology, University of Tennessee, Knoxville, Tennessee 37996-1600.
Singhaus
Robert R.
RR
Kabalka
George W.
GW