Detail of "6940-76-7"

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A general procedure for the enantioselective synthesis of the minor tobacco alkaloids nornicotine, anabasine, and anatabine

All Rights Reserved. A general procedure for the enantioselective synthesis of the minor tobacco alkaloids nornicotine, anabasine, and anatabine. Ayers, Joshua T.; Xu, Rui; Dwoskin, Linda P.; Crooks, Peter A. ( Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, KY, USA). AAPS Journal, 7(3), E752-E758 (English) 2005 American Association of Pharmaceutical Scientists. URL: http://www.aapsj.Some commonly used reagents like 6940-76-7 and 34366-21-7 are used in this experiment.org/articles/aapsj0703/aapsj070375/aapsj070375.pdf . CODEN: AJAOB6. ISSN: 1550-7416. DOCUMENT TYPE: Journal; (online computer file) CA Section: 31 (Alkaloids) Section cross-reference(s): 30 The minor tobacco alkaloids nornicotine, anabasine, and anatabine from Nicotiana tabacum are known to possess nicotinic receptor agonist activity, although they are relatively less potent than S-(-)-nicotine, the principal tobacco alkaloid. Previous pharmacol. investigations and structure-activity studies have been limited owing to the lack of availability of the optically pure forms of these minor alkaloids. A synthetic procedure was reported for the enantioselective synthesis of the optical isomers of nornicotine and anabasine, and a modified procedure for the synthesis of anatabine enantiomers. This procedure involved initial formation of the chiral ketimine resulting from the condensation of either (1R,2R,5R)-(+)- or (1S,2S,5S)-(-)-2-hydroxy-3-pinanone with 3-(aminomethyl)pyridine followed by enantioselective C-alkylation with an appropriate halogenoalkane or halogenoalkene species, N-deprotection, and base-catalyzed intramol. ring closure, to form the appropriate, chirally pure minor tobacco alkaloid. E.g., (S)-(-)-nornicotine (I) was prepd. via enantioselective alkylation/cyclization/elimination reaction of intermediate ketimine II with 1-chloro-3-iodopropane using LDA in THF. Using this approach, the (R)-(+)- and (S)-(-)-enantiomers of the above minor tobacco alkaloids were obtained in good overall chem. yield and excellent enantiomeric excess. .

A convenient synthesis of 1-azabicycloalkanes and their lactams via cuprates of formamidines

A convenient synthesis of 1-azabicycloalkanes and their lactams via cuprates of formamidines. Edwards, Philip D.; Meyers, A. I. (Dep. Chem.Some commonly used reagents like 6940-76-7 is used in this experiment., Colorado State Univ., Fort Collins, CO 80523, USA). Tetrahedron Lett., 25(9), 939-42 (English) 1984. CODEN: TELEAY. ISSN: 0040-4039. DOCUMENT TYPE: Journal CA Section: 27 (Heterocyclic Compounds (One Hetero Atom)) Piperidine and pyrrolidine formamidines, transformed into their a-metallo derivs. are alkylated with bifunctional electrophiles and cyclized, on formamidine removal, to the title compds., e.g. I (n = 1, m = 2; n = m = 1, 2). .