Facile Synthesis of Bioactive Amino Alcohols Utilizing 2-Oxazolone Heterocycle

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Much synthetic potential of 4,5-unsubstituted 2-oxazolone heterocycle has been explored as a versatile builbing block for vic-amino alcohol structures found in a number of biosctive compounds as well as promising leaving moiety if carboxyl and phosphoryl activation processes.1. Chiral Synthons for 1,2-Amino Alcohols : Good verrsatile strategy from such a simple heterocycle to a wide variety of 1,2-amino alcohols has been developed by highyl regio and stereoselective preparation of chiral synthons, 4-methoxy-5-bromo-2-oxazolidinones, followed by stereospecific and stepwise substitution reactions. This methodology is shown highly promising for the efficient preparation of biologically significant hydroxy smino scids such as 4-amino-3-hydroxy-6-methylheptanoic acid (statine), 3-hydroxy-glutamic acid and 4-amino-3- hydroxylutyric acid (GABOB).2. New Synthetic Reagents : The oxazolone-based compounds, aryl bis(2-oxo-3-oxazolinyl) phosphinate and tris(2-oxo-3-oxazolinyl)phosphine oxide, have been newly introduced as excellent reagents for phosphorylation mild enough to benefit fields ranging from phospholipids to polynucleotides and for <bata>-lactam formation from <bata>-amino acids including a facile preparation of the penam, a basic skeleton of penicillins.