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The first synthesis of all possible stereoisomers of the (E)-4,5-dihydroxydec-2-enal, in homochiral form

✍ Scribed by Pietro Allevi; Pierangela Ciuffreda; Giorgio Tarocco; Mario Anastasia

Publisher: Elsevier Science
Year: 1995
Tongue: English
Weight: 465 KB
Volume: 6
Category: Article
ISSN: 0957-4166
DOI: 10.1016/0957-4166(95)00312-d

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✦ Synopsis

The first synthesis of the four possible isomers of (E)-4,5-dihydroxydec-2-enal, a cytotoxic product ofmicrosomal lipid peroxidation, is accomplished starting with D-and Larabinose, 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.

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