Microbiological enantioselective synthesis of (S) and (R) 4-(p-anisyloxy)-3-hydroxybutyrates as new chiral building blocks for the synthesis of β-lactam antibiotics

Banfi, Luca; Cascio, G; Ghiron, Chiara; Guanti, Giuseppe; Manghisi, E.; Narisano, Enrica; Riva, Renata

doi:10.1016/s0040-4020(01)89309-1

Cited by 20 publications

(7 citation statements)

References 46 publications

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“…The resulting anti isomers of N 1 ,N 2 -diprotected α-hydrazino-β-hydroxyesters, containing both hydrazinoalcohol and hydrazinoester moieties, proved to be useful starting materials for the preparation of various important compounds, e.g. aminosugar derivatives [94,95], β-lactam antibiotics [96,97], α-amino-β-hydroxyacids or esters [88,[98][99][100][101][102].…”

Section: Electrophilic Aminations Of Nucleophilic Carbons (Methods F mentioning

confidence: 99%

Chemistry of Hydrazinoalcohols and their Heterocyclic Derivatives. Part 1. Synthesis of Hydrazinoalcohols

Zalán

Lázár

Fülöp

2005

COC

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Hydrazinoalcohols are versatile di-or trifunctional compounds with wide-ranging possibilities for application in organic synthesis. Numerous methods have been devised for the preparation of this family of compounds in recent decades. This review discusses the main pathways for the synthesis of hydrazinoalcohol derivatives, including epoxide ring-openings and nucleophilic substitutions by hydrazines, addition reactions to hydroxyhydrazones, hydrazine additions to olefinic bonds, electrophilic C-and N-amination reactions, cycloadditions, reductions of N-nitroso aminoalcohols and some unique procedures. The latest developments in these fields, involving both conventional and enzymatic catalytic methods of synthetic organic chemistry, allow the highly regio-, stereo-and enantioselective preparation of hydrazinoalcohol derivatives.

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Section: Electrophilic Aminations Of Nucleophilic Carbons (Methods F mentioning

confidence: 99%

Chemistry of Hydrazinoalcohols and their Heterocyclic Derivatives. Part 1. Synthesis of Hydrazinoalcohols

Zalán

Lázár

Fülöp

2005

COC

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“…The starting materials were commercially available b-ketoesters, with the exception of 27, which was synthesized in good overall yield (75% isolated, 94% considering recovered unreacted starting material) by treatment of (p-methoxyphenoxy)acetic acid, previously activated as the imidazolide, with Meldrum acid 15, 27 followed by monodecarboxylation and esterification (Scheme 6). Alkylation of the b-ketoesters was performed following different procedures, in order to achieve the highest yields (Table 1).…”

Section: Resultsmentioning

confidence: 99%

“…R f 0.40 (PE/Et 2 O 85 : 15, b). n max (CHCl 3 )/cm -1 3675, 3610, 3015, 2974, 2931, 1700, 1506, 1474, 1418, 1368, 1230, 1042, 924. d (11), 103 (43), 102 (42), 98 (48), 97 (5.6), 84 (8.2), 73 (6.9), 71 (14), 58 (8.8), 57 (100), 56 (8.0), 55 (15), 43 (69), 41 (27). m/z (ESI -) 269.2124 (M -H + .…”

Section: Tert-butyl 2-octyl-3-oxobutanoate 7bmentioning

confidence: 99%

A new diversity oriented and metal-free approach to highly functionalized 3H-pyrimidin-4-ones

et al. 2011

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A new synthesis of 3H-pyrimidin-4-ones, characterized by four different sets of decorations, is presented. The strategy is based on the synthetic elaboration of readily available α-substituted β-ketoesters that, upon transformation into the corresponding acyl enamines, have been cyclized to give 6H-1,3-oxazin-6-ones. These reactive intermediates have been in turn cleanly converted into highly functionalized pyirimidinones, by treatment with an appropriate primary amine. The whole sequence does not need the use of any metal mediator or catalyst.

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“…[5c, 112] If an itrite was applied as the electrophile, the oxime intermediates 137 were formed, and subsequentr eduction preferentially gave the cis-b-lactams 138 (Scheme 32). [113] Miller and co-workers serendipitously discovered an azide transfer to the C3-position with simultaneous cleavage of the NÀOH bond in the N-hydroxy-b-lactam 139 upon treatment with 4-(azidosulfonyl)benzoic acid in the presence of triethylamine (Scheme 33). [114] Isolation of an intermediate with as ulfonylated hydroxyl group led to the proposal of ap lausible mechanism.…”

Section: -Alkylidene-b-lactamsmentioning

confidence: 99%

Synthetic Approaches toward Monocyclic 3‐Amino‐β‐lactams

et al. 2017

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Due to the emerging resistance against classical β‐lactam‐based antibiotics, a growing number of bacterial infections has become harder to treat. This alarming tendency necessitates continued research on novel antibacterial agents. Many classes of β‐lactam antibiotics are characterized by the presence of the 3‐aminoazetidin‐2‐one core, which resembles the natural substrate of the target penicillin‐binding proteins. In that respect, this Review summarizes the different synthetic pathways toward this key structure for the development of new antibacterial agents. The most extensively applied methods for 3‐amino‐β‐lactam ring formation are discussed, in addition to a few less common strategies. Moreover, approaches to introduce the 3‐amino substituent after ring formation are also covered.

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Microbiological enantioselective synthesis of (S) and (R) 4-(p-anisyloxy)-3-hydroxybutyrates as new chiral building blocks for the synthesis of β-lactam antibiotics

Cited by 20 publications

References 46 publications

Chemistry of Hydrazinoalcohols and their Heterocyclic Derivatives. Part 1. Synthesis of Hydrazinoalcohols

Chemistry of Hydrazinoalcohols and their Heterocyclic Derivatives. Part 1. Synthesis of Hydrazinoalcohols

A new diversity oriented and metal-free approach to highly functionalized 3H-pyrimidin-4-ones

Synthetic Approaches toward Monocyclic 3‐Amino‐β‐lactams

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