The first synthesis of the four possible isomers of (E)-4,5-dihydroxydec-2-enal, a cytotoxic product of microsomal lipid peroxidation, is accomplished starting with D- and L-arabinose, D-ribose and D-lyxose by an identical reaction sequence. Each pentose was diacetonised and subjected to a Wittig reaction for the introduction of a four carbon chain. A selective cleavage of the terminal isopropylidene acetal and the oxidation of the diolic system affords a noraldehyde which is treated with (formylmethylene)triphenylphosphorane to afford the target molecule after regeneration of the diolic system.
THE FIRST SYNTHESIS OF ALL POSSIBLE STEREOISOMERS OF THE (E)-4,5-DIHYDROXYDEC-2-ENAL, IN HOMOCHIRAL FORM / P. ALLEVI, P. CIUFFREDA, G. TAROCCO, M. ANASTASIA. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 6:9(1995), pp. 2357-2364. [10.1016/0957-4166(95)00312-D]
THE FIRST SYNTHESIS OF ALL POSSIBLE STEREOISOMERS OF THE (E)-4,5-DIHYDROXYDEC-2-ENAL, IN HOMOCHIRAL FORM
P. ALLEVIPrimo
;P. CIUFFREDASecondo
;M. ANASTASIAUltimo
1995
Abstract
The first synthesis of the four possible isomers of (E)-4,5-dihydroxydec-2-enal, a cytotoxic product of microsomal lipid peroxidation, is accomplished starting with D- and L-arabinose, D-ribose and D-lyxose by an identical reaction sequence. Each pentose was diacetonised and subjected to a Wittig reaction for the introduction of a four carbon chain. A selective cleavage of the terminal isopropylidene acetal and the oxidation of the diolic system affords a noraldehyde which is treated with (formylmethylene)triphenylphosphorane to afford the target molecule after regeneration of the diolic system.Pubblicazioni consigliate
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