6533b7cffe1ef96bd125984c

RESEARCH PRODUCT

Semisynthesis of new tetrahydrofuranic alkyl ester and furano-pyrone derivatives as inhibitors of the mitochondrial complex I

Almudena BermejoM. Carmen Zafra-poloAdrien CavéEva PerisDiego CortesErnesto EstornellBruno Figadère

subject

chemistry.chemical_classificationAltholactoneStereochemistryOrganic ChemistryBiochemistrySemisynthesisChemical correlationPyroneGoniofupyronechemistry.chemical_compoundchemistryDrug DiscoverySpectral dataAlkylMitochondrial Complex I

description

Abstract Methoxymethylation of altholactone ( 1 ) led to the corresponding O -methoxymethyl derivative ( 3 ) in addition to the unexpected 6,7-dihydro-7-methoxy analogue ( 4 ), and two original tetrahydrofuranic (THF) alkyl esters ( 5 , 6 ). Moreover, when we accomplished a new method for the preparation of the furano-pyrone goniofupyrone ( 7 ) through 7-hydroxylation of 1 in acid medium, a minor compound ( 8 ) with an identical skeleton to that of compounds 5 and 6 was identified. Careful examination of the published spectral data of the reported styryl-lactones with an heptolide skeleton reveals that those structures possess also a THF alkyl ester skeleton. The revision of those structures was confirmed by chemical correlation. All altholactone derivatives assayed proved to be specific inhibitors of the mitochondrial complex I.

yearjournalcountryeditionlanguage
2002-02-01Tetrahedron
https://doi.org/10.1016/s0040-4020(01)01234-0