Synthesis of rigid multivalent scaffolds based on adamantane.
An efficient route to novel 1,3,5,7-tetrasubstituted derivatives of adamantane is described. This route starts from adamantane and gives the tetrafunctionalized derivative 9 in eight steps with an overall yield of 23%. These tetrahedrally shaped molecules possess three identical arms terminated by an activated carboxylic acid derivative and a protected amino function in the 1-position. We propose these tetravalent cage compounds such as 9 as scaffolds for the assembly of ligand/marker conjugates for studies of multivalent ligand receptor interactions. [reaction: see text]
Maison
Wolfgang
W
Universität Hamburg, Institut für Organische Chemie, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany. maison@chemie.uni-hamburg.de
Frangioni
John V
JV
Pannier
Nadine
N
D000218:Adamantane / Q000138:chemical synthesis / Q000737:chemistry*; D008024:Ligands; D008968:Molecular Conformation
D008024:Ligands; D000218:Adamantane