Abstract
All four stereoisomers of coronamic acid were synthesized from both enantiomers of 1,2-butanediol. Cyclopropanation of cyclic sulfate with the dibenzyl malonate anion gave cyclopropane dibenzyl ester in a quantitative yield. Transformation into a protected amino acid was achieved by stereoselective hydrolysis and Curtius rearrangement as the key steps. Saponification and subsequent acidic hydrolysis in one pot and ion exchange gave a free amino acid in a high yield.
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