180295-12-9Relevant academic research and scientific papers
Synthesis of phosphonic acids related to the antibiotic fosmidomycin from allylic α- and γ-hydroxyphosphonates
Oehler, Elisabeth,Kanzler, Silvia
, p. 71 - 90 (2007/10/03)
Pd(0) catalyzed animation of dialkyl (1-methoxycarbonyloxy-2-alkenyl)phosphonates 4 (R3 = H) with the N,O-alkoxycarbonyl protected hydroxylamines BocNHOBoc (3a) and MocNHOMoc (3b) proceeds regiospecifically and with high (E)-stereoselectivity to give the protected (3-N-hydroxyamino-1-alkenyl)-phosphonates 5 and 6, respectively, with very good yields. Alternatively compounds 5 and 6 are obtained in excellent yields from the (3-hydroxy-1-alkenyl)phosphonates 2 under Mitsunobu conditions using 3a and 3b, respectively, as nucleophiles. Much less satisfactory yields of compounds 7 and 8 have been obtained in both pathways using the hydroxylamine derivatives BocNHOBn (3c), and AcNHOAc (3d), respectively, as nucleophiles. Compounds 5-8 have been further transformed to various precursors and analogues of the natural phosphonic acid antibiotics FR 32863 and FR 31564 (fosmidomycin).
