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

CG Bashore, MG Vetelino, MC Wirtz, PR Brooks…

Index: Bashore, Crystal G.; Vetelino, Michael G.; Wirtz, Michael C.; Brooks, Paige R.; Frost, Heather N.; McDermott, Ruth E.; Whritenour, David C.; Ragan, John A.; Rutherford, Jennifer L.; Makowski, Teresa W.; Brenek, Steven J.; Coe, Jotham W. Organic Letters, 2006 , vol. 8, # 26 p. 5947 - 5950

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Citation Number: 14

Abstract

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.