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

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• 作者：Peris ; Eva ; Cavé ; Adrien ; Estornell ; Ernesto ; Zafra-Polo ; M. Carmen ; Figadè ; re ; Bruno ; et. al.
• 关键词：tetrahydrofuran alkyl esters ; furano-pyrones ; styryl-lactones ; mitochondrial complex I inhibitors
• 刊名：Tetrahedron
• 出版年：2002
• 出版时间：February 11, 2002
• 年：2002
• 卷：58
• 期：7
• 页码：1335-1342
• 全文大小：229 K

文摘

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.