Zur Synthese von (±)-cis-1,2-Epoxy-3-oxo-alkyl-phosphonsäureestern—Phosphonomycinanaloga

Treatment of dialkyl-3-oxo-1-alkenylphosphonates1 with OsO₄-H₂O₂ affords the (±)-threo-glycols2, which were characterised as their corresponding diacetates3. The derivatives2 were transformed into the mono-(tert-butyl-dimethylsilylether)-compounds4 and5. Subsequent treatment withp-toluene-sulfonyl chloride yields6 and7, which can be converted to (±)-cis-1,2-epoxy-3-oxoalkylphosphonates8 with tetrabutylammonium fluoride (TBAF). Sometimes thetrans-derivatives9 can be found just as the tosyloxyphosphonates11 and12 as by-products. In two cases the 1,2-dicarbonyl compounds10 were obtained.

Herrn Kollegen Prof. Dr.E. Ziegler zum 70. Geburtstag gewidmet.