Synthesis of bicyclic tertiary alpha-amino acids.
Novel bicyclic alpha-amino acids, exo and endo-1-azabicyclo[2.2.1]heptane-2-carboxylic acid, 1-azabicyclo[2.2.1]heptane-7-carboxylic acid, and 1-azabicyclo[3.2.2]nonane-2-carboxylic acid have been readily synthesized for the generation of neuronal nicotinic receptor ligands. Alkylation of glycine-derived Schiff bases or nitroacetates with cyclic ether electrophiles, followed by acid-induced ring opening and cyclization in NH4OH, allowed for the preparation of substantial quantities of the three tertiary bicyclic alpha-amino acids.
Strachan
Jon-Paul
JP
Targacept, Inc., Winston-Salem, North Carolina 27101-4165, USA.
Whitaker
Regina C
RC
Miller
Craig H
CH
Bhatti
Balwinder S
BS
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000596:Amino Acids; D001643:Bridged Bicyclo Compounds; D002264:Carboxylic Acids