New synthesis of the antibiotic phosphonomycin

EJ Glamkowski, G Gal, R Purick…

Index: Glamkowski,E.J. et al. Journal of Organic Chemistry, 1970 , vol. 35, # 10 p. 3510 - 3512

Full Text: HTML

Citation Number: 80

Abstract

A new, total synthesis of the antibiotic phosphonomycin is described. Thermal rearrangement of di-t-butyl 2-propynyl phosphite yields the di-t-butyl propadienylphosphonate ester. A selective hydrogenation, followed by acid-catalyzed cleavage of the t-butyl groups, affords cis-propenylphosphonic acid in high yield. This olefin acid is epoxidized and the product is resolved in essentially one step to furnish ...