Enantioselective Synthesis of Nicotinic Receptor Probe 7,8-Difluoro-1,2,3,4,5,6- hexahydro-1,5-methano-3-benzazocine
Organic Letters2006Vol. 8(26), pp. 5947–5950
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Crystal G. Bashore, Michael G. Vetelino, Michael Wirtz, Paige R. Brooks, Heather N. Frost, Ruth McDermott, David C. Whritenour, John A. Ragan, Jennifer L. Rutherford, Teresa W. Makowski, Steven J. Brenek, Jotham W. Coe
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.
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