Enantioselective synthesis of nicotinic receptor probe 7,8-difluoro-1,2,3,4,5,6- hexahydro-1,5-methano-3-benzazocine.
[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.
Bashore
Crystal G
CG
Pfizer Global Research and Development, Groton Laboratories, Pfizer Inc., Groton, Connecticut 06340, USA.
Vetelino
Michael G
MG
Wirtz
Michael C
MC
Brooks
Paige R
PR
Frost
Heather N
HN
McDermott
Ruth E
RE
Whritenour
David C
DC
Ragan
John A
JA
Rutherford
Jennifer L
JL
Makowski
Teresa W
TW
Brenek
Steven J
SJ
Coe
Jotham W
JW
D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015335:Molecular Probes; D009538:Nicotine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D011978:Receptors, Nicotinic / Q000737:chemistry*; D013237:Stereoisomerism
C522876:7,8-difluoro-1,2,3,4,5,6- hexahydro-1,5-methano-3-benzazocine; D015335:Molecular Probes; D011978:Receptors, Nicotinic; D009538:Nicotine