Beilstein J. Org. Chem.2014,10, 746–751, doi:10.3762/bjoc.10.69
Abstract A new approach to the anticancer drug Velcade was developed by performing asymmetric borylation of an imine anchored with a chiral N-phosphinyl auxiliary. Throughout the 7-step synthesis, especially in the imine’s synthesis and in the asymmetric borylation reactions, operations and work-up were
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Keywords: asymmetric borylation; GAP chemistry; organophosphorous; N-phosphinylimine; Velcade; Introduction
The synthesis of chiral α-aminoboronic acids and their derivatives has attracted much attention in the organic and medicinal chemistry communities because of their importance for drug discovery and
reported so far [14][15][16][17][18][19][20]. Among the resulting products from the above methods, (R)-(1-amino-3-methylbutyl)boronic acid served as the key mechanism-based pharmacophore in the anticancer drug Velcade, which was the first FDA approved proteasome inhibitor, and has been in clinical use for
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Graphical Abstract
Scheme 1:
Previous work for (R)-(1-amino-3-methylbutyl)boronic acid synthesis.