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

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 t...

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Bibliographic Details
Published in:Tetrahedron 2002-02, Vol.58 (7), p.1335-1342
Main Authors: Peris, Eva, Cavé, Adrien, Estornell, Ernesto, Zafra-Polo, M.Carmen, Figadère, Bruno, Cortes, Diego, Bermejo, Almudena
Format: Article
Language:English
Subjects:
furano-pyrones
mitochondrial complex I inhibitors
styryl-lactones
tetrahydrofuran alkyl esters
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Summary: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. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(01)01234-0