A novel enantioselective synthesis of (S)-(-)- and (R)-(+)-nornicotine via alkylation of a chiral 2-hydroxy-3-pinanone kerimine template

Chirality

Volumn 11, Issue 4, 1999, Pages 316-318

  Swango, Jason H ^a   Bhatti, Balwinder S ^a   Qureshi, Muhammad M ^a   Crooks, Peter A ^a  

^a University of Kentucky   (United States)

Author keywords

Enantiomeric purity; Stereoselective synthesis; Tobacco alkaloids

Indexed keywords

AMMONIUM DERIVATIVE; BROMINE DERIVATIVE; HYDROBROMIC ACID; NORNICOTINE; PYRIDINE DERIVATIVE;

ALKYLATION; ARTICLE; BROMINATION; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; ENANTIOMER; HYDROLYSIS; ISOMERISM; POLYMERIZATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

ALKYLATION; INDICATORS AND REAGENTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NICOTINE; PYRIDINES; STEREOISOMERISM;

EID: 0032944904     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1999)11:4<316::AID-CHIR9>3.0.CO;2-D     Document Type: Article

References (14)

1. Holmstedt, B. The use of enantiomers in biological studies: an historical review. In: Frank H, Holmstedt B, Testa B, editors. Chirality and biological activity. New York: Alan R. Liss; 1990. p 1-14.
2. Copeland JR, Adem A, Jacob III P, Nordberg A. A comparison of the binding of nicotine and nornicotine stereoisomers to nicotinic binding sites in rat brain cortex. Naunyn-Schmiedeberg's Arch Pharmacol 1991;343:123-127.
3. Kisaki T, Tamaki E. Phytochemical studies on the tobacco alkaloids. X. Degradation of the tobacco alkaloids and their optical rotatory changes in tobacco plants. Phytochemistry 1966;5:293-300.
4. Dwoskin LP, Buxton ST, Jewell AL, Crooks PA. (S)-(-)-nornicotine increases dopamine release in a calcium-dependent manner from superfused rat striatal slices. J Neurochem 1993;60:2167-2174.
5. Crooks PA, Dwoskin LP. Contribution of CNS nicotine metabolites to the neuropharmacological effects of nicotine and tobacco smoking. Biochem Pharmacol 1996;54:743-753.
6. Bardo MT, Bevins RA, Klebaur JE, Crooks PA, Dwoskin PL. (-)-Nornicotine partially substitutes for (+)-amphetamine in a drug discrimination paradigm in rats. Pharmacol Biochem Behav 1997;58: 1083-1087.
7. Dwoskin LP, Crooks PA, Marion MB, Bardo MT. Behavioral sensitization to nornicotine enantiomers: cross-sensitization to nicotine. Psychopharmacology. In press.
8. Jacob III P. Resolution of (+/-)-5-bromonornicotine. Synthesis of (R)- and (S)-nornicotine of high enantiomeric purity. J Org Chem 1982;47: 4165-4167.
9. Seeman JI, Chavdarian CG, Secor HV. Synthesis of the enantiomers of nornicotine. J Org Chem 1985;50:5419-5421.
10. Mahboodi S, Wiegrebe W. Enantioselective synthesis of some Nicotiana alkaloids. Arch Pharm 1988;321:175-177.
11. Joyce NJ, Leete E. The formation of 1-methyl-3-nicotinoylpyrrolidine from nicotine-1′-oxide. Heterocycle 1989;29:1335-1342.
12. 1H-NMR spectroscopy in the presence of 1,1′-binaphthyl-2,2′-diylphosphoric acid. Chirality 1996;8:295-299.
13. Aiqiao M, Xiao X, Lanjun W, Yaozhong J. Asymmetric synthesis XV: enantioselective syntheses of (R) or (S)-α-substituted-(2-pyridyl) methylamines via chiral pinanone ketimine template. Synth Commun 1991;21:2207-2212.
14. Carlson R, Pierce J. The synthesis and stereochemistry of the four isomeric pinane-2,3-diols. J Org Chem 1971;36:2319-2324.-