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Synlett 1996; 1996(10): 981-982
DOI: 10.1055/s-1996-5646
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Synthesis of (±)-Indolizidine 209B and a New 209B Diastereoisomer

Joseph P. Michael* , David Gravestock
  • *Centre for Molecular Design, Department of Chemistry, University of the Witwatersrand, P. O. Wits 2050, South Africa, Fax (+ 27) 11 339 7967, E-mail jmichael@aurum.chem.wits.ac.za
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Publication Date:
31 December 2000 (online)

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Eight-step syntheses of the frog skin toxin (±)-indolizidine 109B (1) and its hitherto unknown (5R*,8S*,9S*) diastereoisomer (14) via vinylogous urethane intermediates are described. Control of the relative stereochemistry is achieved by alternative stereoselective reductions of a common intermediate, the bicyclic vinylogous urethane 9.

alkaloid - enaminone - indolizidine - sulfide contraction - vinylogous urethane

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