Journal of the American Chemical Society

Biomimetic synthesis of anatabine from 2, 5-dihydropyridine produced by the oxidative decarboxylation of baikiain

E Leete, ME Mueller

Index: Leete; Mueller Journal of the American Chemical Society, 1982 , vol. 104, # 23 p. 6440 - 6444

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Citation Number: 22

Abstract

Abstract: The tobacco alkaloid anatabine (1, 2, 3, 6-tetrahydr0-2, 3'-bipyridine) is formed, along with small amounts of pyridine and glutaconaldehyde, when baikiain (1, 2, 3, 6- tetrahydropyridine2-carbxylic acid) is oxidized with sodium hypochlorite. Baikiain, labeled with deuterium or 13C at C-2, yielded anatabine labeled only at the C-2 and C-2'positions, the location of the isotopes being determined by NMR spectroscopy. The formation of ...

~25%

Total synthesis of (S)-anabasine and (S)-anatabine

[Felpin; Vo-Thanh; Robins; Villieras; Lebreton Synlett, 2000 , # 11 p. 1646 - 1648]

Metabolism of N-alkyldiamines and N-alkylnortropinones by tr...

[Boswell, Henry D.; Draeger, Birgit; Eagles, John; McClintock, Carol; Parr, Adrian; Portsteffen, Andreas; Robins, David J.; Robins, Richard J.; Walton, Nicholas J.; Wong, Chi Phytochemistry, 1999 , vol. 52, # 5 p. 855 - 869]