169889-40-1Relevant academic research and scientific papers
Stereoselective Oxygenation of the Homotropane Ring System; Synthesis of Exo- and Endo-7-Hydroxy- and 7,8-Epoxyhomotropanes
Justice, David E.,Malpass, John R.
, p. 4685 - 4688 (1995)
Stereoselective introduction of an endo- epoxide into the 2-carbon bridge of the homotropane (9-azabicyclononane) ring system has been achieved via a 4-aminocyclooct-2-enol derivative; the direct route to the exo- analogue from 7,8-dehydrohomotropa
Synthesis and nicotinic acetylcholine-binding properties of epibatidine homologues: Homoepibatidine and dihomoepibatidine
Malpass,Hemmings,Wallis,Fletcher,Patel
, p. 1044 - 1050 (2007/10/03)
Homoepibatidine 2 and dihomoepibatidine 3 have been synthesised from the 8-azabicyclo[3.2.1]oct-6-ene 8 and the 9-azabicyclo[4.2.1]oct-7-ene 9, respectively, the key precursors for reductive Heck coupling reactions. Alternative routes starting from cyclohepta- and cycloocta-1,3-diene are described; deoxygenation of tropane and homotropane epoxides provides a convenient route to 8 and 9. The enantiomers of 2 show similar potency at nicotinic receptors to the corresponding epibatidine enantiomers; the affinity of 3 is lower.
