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On the formation of reductic acid from pentoses or hexuronic acids

✍ Scribed by Tania Ahmad; Rolf Andersson; Kjell Olsson; Eric Westerlund

Publisher: Elsevier Science
Year: 1993
Tongue: English
Weight: 452 KB
Volume: 247
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(93)84254-4

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✦ Synopsis

ABSTRAa

Careful hydrolysis of (+ kis-or (+ )-trans-tetrahydro-2,5-dimethoxy-2-furaldehyde dimethyl acetal proceeded via 5,5-dimethoxy-4-oxopentanal to give (+ )-tram-4-hydroxy-5-methoxy-2-cyclopentenone and ( f )-rrans-4,5-dihydroxy-2qclopentenone.

The latter product did not isomerize to 2,3-dihydroxy-2qclopentenone (reductic acid) on prolonged reaction.

Scheme 1. Proposed formation mechanism of reductic acid.

* Corresponding author. ' All chiral compounds were obtained as racemic mixtures, but only one enantiomer is shown.

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