Synthesis of novel unsaturated AE-bicyclic analogues of lycoctonine, inuline and methyllycaconitine: With olefinic J = 13.5 Hz, but still cis
Trigg WJ., Grangier G., Lewis T., Rowan MG., Potter BVL., Blagbrough IS.
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).