Open-cyclic warfarin isomerism: 5-hydroxywarfarin

B Castleberry, EJ Valente, DS Eggleston

Index: Castleberry, Brian; Valente, Edward J.; Eggleston, Drake S. Journal of Crystallographic and Spectroscopic Research, 1990 , vol. 20, # 6 p. 583 - 593

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Citation Number: 9

Abstract

Abstract Addition of a 5-hydroxy substituent to warfarin [3-(1-phenyl-3-oxobutyl)-4- hydroxycoumarin] shifts the solution equilibrium in chloroform to favor the open isomeric form over the two cyclic diastereomeric hemiketals. X-ray diffraction analysis reveals 5- hydroxywarfarin crystallizes as the open isomer in contrast to the more than 20 warfarin and analog structures which occur as cis or trans hemiketal forms in the solid. The two peri ...