Enantioselective Synthesis of Nicotinic Receptor Probe 7,8-Difluoro-1,2,3,4,5,6- hexahydro-1,5-methano-3-benzazocine

Abstract

[Structure: see text] The development of a concise enantioselective synthesis of nicotinic alkaloid 1 is presented. The route features the synthesis and use of a "stable" aliphatic triflate 21 in an alkylation step to generate Heck precursor 24 and an enantioselective cyclization to establish a compound with the key [3.2.1]-bicyclic core, 29.