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 subjec...

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Published inJournal of organic chemistry Vol. 62; no. 13; pp. 4476 - 4478
Main Authors Srivastava, Rajiv R, Singhaus, Robert R, Kabalka, George W
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 27.06.1997
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Summary: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.
Bibliography:ark:/67375/TPS-BFDXGS8Q-Z
istex:2F72E5BCFF8C5AEDABB8D90357D2BAB2164FE89A
Abstract published in Advance ACS Abstracts, June, 1; 1997.
ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo970148+