SYNTHESIS OF PHOSPHONIC ACIDS RELATED TO THE ANTIBIOTIC FOSMIDOMYCIN FROM ALLYLIC α- AND γ-HYDROXYPHOSPHONATES

1 May 1996

journal article
research article
Published by Taylor & Francis in Phosphorus, Sulfur, and Silicon and the Related Elements

Vol. 112 (1-4) , 71-90
https://doi.org/10.1080/10426509608046350

Abstract

Pd(O) catalyzed amination 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-l-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).

Keywords

This publication has 37 references indexed in Scilit:

Synthesis of N-Hydroxy α-Amino Acids from α-Hydroxy Acids with High Enantiomeric Purity
Synlett, 1995
N- and O-acyl derivatives of Deoxy-N-hydroxyaminosugars
Advanced Synthesis & Catalysis, 1994
Design and synthesis of achiral 5-lipoxygenase inhibitors employing the cyclobutyl group
Bioorganic & Medicinal Chemistry Letters, 1993
Studies on Organophosphorus Compounds; LXXV: A Facile Synthesis of 1-(Hydroxyamino)alkyl(or aryl)phosphonic Acids
Synthesis, 1993
Solid films and layers deposited on silicon — a versatile infrared sampling technique
Vibrational Spectroscopy, 1992
BIOLOGICAL ACTIVITY OF AMINOPHOSPHONIC ACIDS
Phosphorus, Sulfur, and Silicon and the Related Elements, 1991
Zur Reaktion von Dialkylphosphiten mit α‐Enonen, I Synthese und Allyl‐Umlagerung von (1‐Hydroxy‐2‐alkenyl)‐ und (1‐Hydroxy‐2‐cycloalkenyl)phosphonsäure‐dimethylestern
European Journal of Inorganic Chemistry, 1991
Studies on phosphonic acid antibiotics. IV. Synthesis and antibacterial activity of analogs of 3-(N-acetyl-N-hydroxyamino)-propylphosphonic acid (FR-900098).
CHEMICAL & PHARMACEUTICAL BULLETIN, 1982
Studies on phosphonic acid antibiotics. III. Structure and synthesis of 3-(N-acetyl-N-hydroxyamino)propylphosphonic acid (FR-900098) and 3-(N-acetyl-N-hydroxyamino)-2(R)-hydroxypropylphosphonic acid (FR-33289)
CHEMICAL & PHARMACEUTICAL BULLETIN, 1981
Reaktionen mit phosphororganischen Verbindungen, XLIV Darstellung von 3‐Oxo‐1‐alkenylphosphonsäure‐dialkylestern
European Journal of Organic Chemistry, 1979