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Synlett 2000; 2000(11): 1646-1648
DOI: 10.1055/s-2000-7907
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Total Synthesis of (S)-Anabasine and (S)-Anatabine

François-Xavier Felpin* , Giang Vo-Thanh, Richard J. Robins, Jean Villiéras, Jacques Lebreton
  • *Laboratoire de Synthèse Organique, CNRS UMR 6513, Faculté des Sciences et des Techniques, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France
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Publication Date:
31 December 2000 (online)

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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.

piperidine alkaloid - asymmetric synthesis - allylboration - ring closing metathesis - ruthenium