Regioselective synthesis of the 1-bromo-4-phenyl-tetrahydro-7-amino-benzocyclohepten-6-one, a subnanomolar aminopeptidase-N/CD13 inhibitor
M Al-Lakkis-Wehbe, L Roux, C Charrier, S Alavi…
Index: Al-Lakkis-Wehbe, Mira; Roux, Lionel; Charrier, Cedric; Alavi, Sarah; Le Nouen, Didier; Defoin, Albert; Tarnus, Celine; Albrecht, Sebastien Tetrahedron, 2012 , vol. 68, # 32 p. 6447 - 6455
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Citation Number: 5
Abstract
A regioselective synthesis of the title 1-bromo-4-phenyl-tetrahydro-7-amino- benzocyclohepten-6-one 2 has been pursued and develop in order to allow a large scale synthesis of this highly potent and selective APN inhibitor (Ki 60 pM). The pivotal step in this approach was the desymmetrization of the ketones 6a, b through regioselective generation of the silyl enol ethers 5a, b. After obtention of the corresponding enones 13a, b and the ...