Structuralmodificationofent-kauranediterpenoidsbyatom transfer radicaladditions

Gîrbu Vladilena; Pruteanu Elena; Ungur Nikon; Kulciţki Veaceslav; Renaud Philippe

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GÎRBU, Vladilena, PRUTEANU, Elena, UNGUR, Nikon, KULCIŢKI, Veaceslav, RENAUD, Philippe. Structuralmodificationofent-kauranediterpenoidsbyatom transfer radicaladditions. In: Trends in Organic Synthesis: 2017 Villars Summer School, 27-31 iulie 2017, Villars-sur-Ollon. Villars-sur-Ollon, Switzerland: École Polytechnique Fédérale de Lausanne, 2017, p. 66.

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Trends in Organic Synthesis 2017

Colocviul "Trends in Organic Synthesis"
Villars-sur-Ollon, Switzerland, 27-31 iulie 2017

Structuralmodificationofent-kauranediterpenoidsbyatom transfer radicaladditions

Pag. 66-66

Gîrbu Vladilena¹², Pruteanu Elena¹², Ungur Nikon¹, Kulciţki Veaceslav¹, Renaud Philippe³

¹ Institute of Chemistry of the Academy of Sciences of Moldova,
² University of the Academy of Sciences of Moldova,
³ University of Bern

Disponibil în IBN: 30 iulie 2020

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Ent-kaurane-typediterpenoidsarewidespreadinnumerousplantsources[1]andsome
representativesarereadilyavailableforlargescaleisolation.Themostknown
examplesareperhapsent-kaurenoicacid1andsteviol2,whichcanbeconveniently
isolatedfrom industrialcrops,derivedproductsorresiduesofagriculture.
Thesenaturalcompoundsalonepossessavarietyofinterestingbiologicalproperties
and also a lotofSAR studies have been reported basing on theirstructural
modification[2].Surprisingly,thereactivityoftheexo-methylenicΔ16,17 doublebond
wasmostlyaddressedbasingonheteroatom additionandoxidativetransformations.
We focused ourattention on applying radicalprocesses to complex natural
structuresasrealusefultoolsforexpandingmolecularcomplexityandsynthesisof
newbiologicallyactivecompounds.Severaltransformationshavebeeninvestigated
withbothent-kaurenoicacid1andsteviol2,aswellaswiththerelated15-hydroxyent-
kaurenoic acid 3.It included radicalhydroazidation,carboazidation and
carboiodination[3].Thederivedproducts,inparticularazidessuchas4and5,have
beenusedtogenerateaseriesoffunctionalizedent-kauranesforSARstudies.
Acknowledgements
The presented work was performed within the project “Radical mediated
modifications ofnaturalproducts”supported financiallybythe Swiss National
ScienceFoundation(SCOPESprogram,projectNo.IZ73Z0_152346/1).
References
[1]Ghisalberti,E.L.Fitoterapia,1997,63,303.
[2]Morarescu,O.ChemistryJournalofMoldova,2015,10(1),9-19.
[3]Lapointe,G.,Kapat,A.,Weidner,K.,Renaud,P. Pureandappliedchemistry, 2012,84(7),1633-1641.

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