Synthesis, Stability, and Antimicrobial Activity of (+)-Obafluorin and Related. beta.-Lactone Antibiotics

Y Pu, C Lowe, M Sailer, JC Vederas

Index: Pu, Yunlong; Lowe, Christopher; Sailer, Miloslav; Vederas, John C. Journal of Organic Chemistry, 1994 , vol. 59, # 13 p. 3642 - 3655

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Citation Number: 34

Abstract

L-threonine-@-lactone (21) was transformed to a series of N-acylated derivatives including the following: 22d (2, 3-dihydroxybenzoyl), 26 (2-hydroxybenzoyl), 27 (3, 4- dihydroxybenzoyl), 29 (4'-methyl-2, 2'-bipyridine-4-carbonyl), 31 (c-(ba-aminoadipoyl)), 34 ((N'-2, 3-dihydroxybenzoyl)-@-alanyl), 36 (bromoacetyl), 36 ((6-purinylthio) acetyl), and 37 ((4-pyridy1thio) acetyl). The results show that a-amino@-lactones bearing an N-acyl group ...