Planta Med 2012; 78 - CL19
DOI: 10.1055/s-0032-1320254

Synthesis of small library of secologanin analogs starting from sweroside and oleuropein

H Lemoine 1, B Deguin 1
  • 1Laboratoire de Pharmacognosie de l'Université Paris Descartes, Sorbonne Paris Cité UMR/CNRS 8638, Faculté des Sciences Pharmaceutiques et Biologiques 4, Avenue de l'Observatoire, 75006, Paris

Dedicated to the memory of Pr François Tillequin

Secologanin 1 and sweroside 2 were isolated on preparative scale from Lonicera tatarica (Caprifoliaceae) by a new isolation process. Perpivaloylsweroside 3 was converted into secologanin 1, via a novel sequential three-step procedure, followed by deprotection. This new methodology was successfully applied on sweroside analogs and afforded four enantiopure secologanin analogs 4–5. Furthermore the abundant secoiridoid oleuropein 6 extracted from Olea europea (Oleaceae) was converted into 9-dehydro-10-(H)-secologanin 7. This small library of secologanin analogs can be used as starting materials in total synthesis of natural product analogs.