Synthesis of the first highly potent bridged nicotinoid 9-azabicyclo [4.2. 1] nona [2, 3-c] pyridine (pyrido [3, 4-b] homotropane)

DB Kanne, DJ Ashworth, MT Cheng…

Index: Kanne; Ashworth; Cheng; et al. Journal of the American Chemical Society, 1986 , vol. 108, # 24 p. 7864 - 7865

Full Text: HTML

Citation Number: 37

Abstract

3b (s-trans) 38 (s-cis) a potent agonist in its own right, has an activity significantly less than that of anatoxin a. 4 The present work was prompted by the recognition that one of the conformers of nornicotine would position the pyrrolidine nitrogen and a hydrogen-bond acceptor in the same spacial orientation as that found in the s-cis conformation (%) of anatoxin a. The H-bond acceptor of 2 (pyridine nitrogen lone pair) corresponds ...