An efficient, one-pot synthesis of fosfomycin dialkyl esters from (R)-2-tosyloxypropanal
(R)-2-Tosyloxypropanal (4) was prepared from D-mannitol in a 7-step sequence (51% overall yield). Addition of dialkyl phosphonates to 4 in the presence of titanium isopropoxide and the subsequent treatment with DBU stereoselectively afforded, in one-pot, fosfomycin dimethyl (5a) and dibenzyl (5b) esters both in 58% isolated yield.
Sharpless asymmetric dihydroxylation of trans-propenylphosphonate by using a modified AD-mix-α and the synthesis of fosfomycin
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Kobayashi,William,Tokoro
p. 7903 - 7906
(2007/10/03)
Silicon Directed Asymmetric Synthesis of (1R,2S)-(-)-(1,2-Epoxypropyl)phosphonic Acid (Fosfomycin) from (S)-Lactaldehyde
The title compound is obtained in high diastereomeric purity based on the stereoselective addition of trimethylsilyldibenzylphosphite (TMSDBP) to O-triisopropylsilyloxy (S)-lactaldehyde.