- Regioselective palladium(0) catalyzed amination of carbonates of allylic α-hydroxyphosphonates with hydroxylamine derivatives: A convenient route to phosphonic acids related to the antibiotic fosmidomycin
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Palladium(0) catalyzed amination of diisopropyl (1-methoxycarbonyloxy-2-propenyl)phosphonate (1) with tert-butyl (tert-butoxycarbonyloxy)carbamate (BocNHOBoc, 2a), and (N-acetyloxy)acetamide (AcNHOAc, 2b) proceeds regiospecifically and with high (E)-stereoselectivity to give the protected [3-(N-hydroxyamino)-1-propenyl]phosphonates 3a and 3b, respectively, in high yields. Hydrogenation of compounds 3a and 3b affords the corresponding propylphosphonates 4. Compounds 3a,b and 4a,b are further converted to precursors and analogues of the phosphonic acid antibiotic fosmidomycin.
- Ohler,Kanzler
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Read Online
- Fosmidomycin analogues as inhibitors of monoterpenoid indole alkaloid production in Catharanthus roseus cells
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Substituted 3-[2-(diethoxyphosphoryl)propyl]oxazolo[4,5-b]pyridine-2(3H)- ones were obtained by functionalization at 6-position with various substituents (aryl, vinyl, carbonyl chains) via reactions catalysed with palladium. We found that these new fosmidomycin analogues inhibited the accumulation of ajmalicine, a marker of monoterpenoid indole alkaloids production in plant cells. Some of them have greater inhibitory effect than fosmidomycin and fully inhibit alkaloid accumulation at the concentration of 100 μM.
- Mincheva, Zoia,Courtois, Martine,Andreu, Francoise,Rideau, Marc,Viaud-Massuard, Marie-Claude
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p. 1797 - 1803
(2008/02/02)
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- Use of organophosphorus compounds for the therapeutic and prophylactic treatment of infections
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Use of organophosphorus compounds of general Formula (I) for the therapeutic and prophylactic treatment of infections in humans and animals caused by viruses, fungi and parasites.
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Page column 14
(2010/02/05)
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- N-(Diethoxyphosphoryl)-O-benzylhydroxylamine - A convenient substrate for the synthesis of N-substituted O-benzylhydroxylamines
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Easily available N-(diethoxyphosphoryl)-O-benzylhydroxylamine was shown to be convenient, orthogonally protected substrate for regioselective N-alkylation by means of diverse halides under basic conditions (sodium hydride/ tetrabutylammonium bromide). An
- B?azewska, Katarzyna,Gajda, Tadeusz
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p. 10249 - 10254
(2007/10/03)
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- Hydroxyaminohydrocarbonphosphonic acids
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New hydroxyaminohydrocarbonphosphonic acid derivatives of the formula: STR1 wherein R1 is hydrogen or acyl, R2 is hydrogen, lower alkyl, ar(lower)alkyl or acyl, and A is lower alkylene, lower alkenylene or hydroxy(lower)alkylene, or
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- STUDIES ON PHOSPHONIC ACID ANTIBIOTICS. I. STRUCTURE AND SYNTHESIS OF 3-(N-ACETYL-N-HYDROXYAMINO)PROPYLPHOSPHONIC ACID (FR-900098) AND ITS N-FORMYL ANALOGUE (FR-31564)
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The structure elucidation of FR-900098 (1) isolated from a microorganism source and the syntheses of FR-900098 and its N-formyl analogue, FR-31564 (2), are described.The latter possesses a superior antimicrobial activity.
- Kamiya, Takashi,Hemmi, Keiji,Takeno, Hidekazu,Hashimoto, Masashi
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