51787-59-8Relevant academic research and scientific papers
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.
Synthesis of epibatidine homologues: Homoepibatidine and bis- homoepibatidine
Malpass,Hemmings,Wallis
, p. 3911 - 3914 (2007/10/03)
Synthetic approaches are described leading to homoepibatidine and bis- homoepibatidine which are based, respectively, on the tropane (8- azabicyclo[3.2.1]octane) and homotropane (9-azabicyclo-[4 2.1]nonane) ring systems. Epoxy- tropanes and -homotropanes (which are readily available from simple cyclic dienes) are convenient precursors for the azabicyclic alkenes needed for the key reductive coupling with pyridine derivatives.
