The Yb(OTf)3 catalyzed Biginelli cyclocondensation reaction of 3-hydroxybenzaldehyde, ethyl acetoacetate and thiourea afforded the corresponding dihydropyrimidine-2-thione, called monastrol, in 95% isolated yield. The chiral resolution of racemic monastrol, a mitosis blocker by kinesin Eg5 inhibition, was carried out on a preparative scale (ca. 100 mg) through diastereomeric N-3 ribofuranosyl amides.
Improved synthesis and preparative scale resolution of racemic monastrol / Dondoni, A.; Massi, A.; Sabbatini, Simona. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - STAMPA. - 43:(2002), pp. 5913-5916. [10.1016/S0040-4039(02)01269-8]
Improved synthesis and preparative scale resolution of racemic monastrol.
SABBATINI, Simona
2002-01-01
Abstract
The Yb(OTf)3 catalyzed Biginelli cyclocondensation reaction of 3-hydroxybenzaldehyde, ethyl acetoacetate and thiourea afforded the corresponding dihydropyrimidine-2-thione, called monastrol, in 95% isolated yield. The chiral resolution of racemic monastrol, a mitosis blocker by kinesin Eg5 inhibition, was carried out on a preparative scale (ca. 100 mg) through diastereomeric N-3 ribofuranosyl amides.File in questo prodotto:
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