Synthesis of phosphonic acids related to the antibiotic fosmidomycin from allylic α- and γ-hydroxyphosphonates

Article abstract of DOI:10.1080/10426509608046350

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).

Full text of DOI:10.1080/10426509608046350

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Phosphorus, Sulfur, and Silicon and the
Related Elements
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SYNTHESIS OF PHOSPHONIC ACIDS
RELATED TO THE ANTIBIOTIC
FOSMIDOMYCIN FROM ALLYLIC α- AND γ-
HYDROXYPHOSPHONATES
Elisabeth Öhler a & Silvia Kanzler a
a Institut für Organische Chemie der Universität Wien , Währinger
Straβe 38, A-1090, Wien, Austria
Published online: 04 Oct 2006.
To cite this article: Elisabeth Öhler & Silvia Kanzler (1996) SYNTHESIS OF PHOSPHONIC ACIDS RELATED
TO THE ANTIBIOTIC FOSMIDOMYCIN FROM ALLYLIC α- AND γ-HYDROXYPHOSPHONATES, Phosphorus,
Sulfur, and Silicon and the Related Elements, 112:1-4, 71-90, DOI: 10.1080/10426509608046350
To link to this article: http://dx.doi.org/10.1080/10426509608046350
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