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Planta Med 2012; 78 - CL19
DOI: 10.1055/s-0032-1320254
DOI: 10.1055/s-0032-1320254
Synthesis of small library of secologanin analogs starting from sweroside and oleuropein
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.