Practical Synthesis of Optically Pure 1- and 3-Substituted Dihydroorotic Acids

Mamoru SUZUKI; Hiroshi MAEDA; Kazuhiko KONDO; Hiroshi SUGANO; Kazuo MATSUMOTO

doi:10.1248/cpb.37.1764

Mamoru SUZUKI, Hiroshi MAEDA, Kazuhiko KONDO, Hiroshi SUGANO, Kazuo MATSUMOTO

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Keywords: dihydroorotic acid, benzyl dihydroorotate, substituted dihydroorotic acid, alkylation, Mitsunobu reaction, quinidine, optical resolution

JOURNAL FREE ACCESS

1989 Volume 37 Issue 7 Pages 1764-1769

DOI https://doi.org/10.1248/cpb.37.1764

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Abstract

Various optically pure 3-substituted dihydroorotic acids (9, 12) were synthesized by the N-alkylation and Mitsunobu reaction of optically active benzyl or tert-butyl dihydroorotate (6, 10), followed by deprotection of the ester group.Moreover, optically pure 1-methyl (16, 17) and 1-ethyl (19) dihydroorotic acids were obtained by an optical resolution method.

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