✦ LIBER ✦

Synthesis of 13C warfarin labelled at the hemiketal carbon, and its resolution

✍ Scribed by Van Henry Savell Jr.; Edward J. Valente; D. S. Eggleston

Publisher: John Wiley and Sons
Year: 1989
Tongue: French
Weight: 198 KB
Volume: 27
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580270605

No coin nor oath required. For personal study only.

✦ Synopsis

2-hydroxy-2-methyl-4-phenyl-3,4-dihydro-2€J,5~pyrano[3,2-cl[l]benzopyran-5-one IS labeled with 98+% 13C at the anomeric carbon (C2) and resolved 4-phenyl-3-buten-2-one-2-13C(98+%). Michael-type addition of this to 4-hydroxycoumarin in methanol produces the labeled diastereomeric warfarin methyl ketals which on deprotection form racemic ~arfarin-2-~~C(98+%). Classical resolution of labeled warfarin with quinidine produces partly resolved (S)-(-)-warfari11-2-'~C(98+%). Labeled warfarin is a suitable probe for warfarin configuration for which three distinct isomeric forms are known.

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