The LFA-1 inhibitor and leukocyte adhesion suppressor BIRT-377 was prepared in high enantiomeric excess by desymmetrization of dimethyl 2-p-bromobenzyl-2-methylmalonate, followed by condensation of the resulting carboxylic acid with 3,5-dichloroaniline, saponification of the remaining ester and Curtius rearrangement as the key steps. When Curtius rearrangement preceded the condensation step, (ent)-BIRT-377 was similarly obtained in high ee.
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Acta Crystallogr E Crystallogr Commun
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University of South Alabama, Department of Chemistry 6040 USA Drive South Mobile Alabama 36608 USA.
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View Article and Find Full Text PDFArticle Synopsis
- * This study presents the first successful synthesis of cobaltacarborane compounds with one or two primary amino groups directly bonded to carbon atoms, using azide reductions or Curtius rearrangements.
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Institutes of Organic and Inorganic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.
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