Synthesis of novel unsaturated AE-bicyclic analogues of lycoctonine, inuline and methyllycaconitine: with olefinic J = 13.5 Hz, but still cis

We have synthesised unsaturated AE-bicyclic analogues of lycoctonine class norditerpenoid alkaloids by acetylide addition and regiochemically controlled reductions. Reduction of a substituted propargylic alcohol with hydrogen gas (poisoned Pd catalyst) gave an alkene with vicinal J = 13.5 Hz. This w...

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Published in:Tetrahedron letters 1998-02, Vol.39 (8), p.893-896
Main Authors: Trigg, William J., Grangier, Géraldine, Lewis, Terence, Rowan, Michael G., Potter, Barry V.L., Blagbrough, Ian S.
Format: Article
Language:English
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Summary:We have synthesised unsaturated AE-bicyclic analogues of lycoctonine class norditerpenoid alkaloids by acetylide addition and regiochemically controlled reductions. Reduction of a substituted propargylic alcohol with hydrogen gas (poisoned Pd catalyst) gave an alkene with vicinal J = 13.5 Hz. This was shown to be of Z-geometry by unambiguously preparing the corresponding E-alkene ( J = 15.4 Hz). Novel unsaturated AE-bicyclic analogues of the potent nicotinic receptor antagonist methyllycaconitine have been prepared. A cis-vicinal J=13.5Hz was measured, extending the range of acceptable coupling constants in cis-alkenes. [Display omitted]
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(97)10649-9