Synlett

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

…, G Vo-Thanh, RJ Robins, J Villiéras, J Lebreton

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

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Citation Number: 21

Abstract

Abstract: A chiral synthesis of (S)-anabasine and (S)-anatabine from 3- pyridinecarboxaldehyde, via a ring closing metathesis reaction (RCM) as the key step, is reported in 8 steps for both products with overall yields of 35% and 30%, respectively. Key words: piperidine alkaloid, asymmetric synthesis, allylboration, ring closing metathesis, ruthenium

~70%

~92%

Biomimetic synthesis of anatabine from 2, 5-dihydropyridine ...

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

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]