Enantiospecific and diastereoselective synthesis of cis monobactams through electrophilic amination of chiral 3-hydroxyesters

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

doi:10.1016/s0040-4020(01)89308-x

Cited by 18 publications

(6 citation statements)

References 74 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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“…Our initial efforts to prepare the desired 3-amino-4-substituted monocyclic ß-lactams through N1–C4 ring closure reactions (e.g., via Mitsunobu cyclization [ 31 ] or bromine-induced cyclization [ 32 ]) were unproductive. In a subsequent approach, the convergent methodology for the stereoselective synthesis of functionalized β-lactams with a broad substrate scope developed by Staudinger et al [ 20 ] was explored.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 3-Amino-4-substituted Monocyclic ß-Lactams—Important Structural Motifs in Medicinal Chemistry

Grabrijan

Strašek

Gobec

2021

IJMS

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Monocyclic ß-lactams (azetidin-2-ones) exhibit a wide range of biological activities, the most important of which are antibacterial, anticancer, and cholesterol absorption inhibitory activities. The synthesis of decorated monocyclic ß-lactams is challenging because their ring is highly constrained and consequently reactive, which is also an important determinant of their biological activity. We present the optimized synthesis of orthogonally protected 3-amino-4-substituted monocyclic ß-lactams. Among several possible synthetic approaches, Staudinger cycloaddition proved to be the most promising method for initial ring formation, yielding monocyclic ß-lactams with different substituents at the C-4 position, a phthalimido-protected 3-amino group, and a (dimethoxy)benzyl protected ring nitrogen. Challenging deprotection methods were then investigated. Oxidative cleavage with cerium ammonium nitrate and ammonia-free Birch reduction was found to be most effective for selective removal of ring nitrogen protection. Hydrazine hydrate was used for deprotection of the phthalimido group, and the procedure had to be modified by the addition of HCl in the case of aromatic substituents at the C-4 position. The presented methods and the synthesized 3-amino-4-substituted monocyclic ß-lactam derivatives are an important step toward new ß-lactams with potential pharmacological activities.

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“…Known alcohol 4 , which was prepared from 1,3-propanediamine in 36% yield, was reacted with N -Alloc- N -Ns amine 5 under Mitsunobu conditions (DEAD, PPh 3 , PhH, rt) to give trimer triamine 6 in 79% yield (Scheme ). The exposure of the trityl ether 6 to TsOH in MeOH gave trimer alcohol 7 in 85% yield, which was ready to couple with the heterotricycle fragment.…”

Section: Results and Discussionmentioning

confidence: 99%

Total Synthesis of the Proposed Structure for Protoaculeine B, a Polycationic Marine Sponge Metabolite, with a Homogeneous Long-Chain Polyamine

et al. 2020

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By establishing the procedures for sequential deprotections, reaction monitoring, purification, and handling, for the first time, we achieved the total synthesis of the proposed structure for protoaculeine B (2), which is a highly hydrophilic and polycationic amino acid. The NMR and mass spectra and chemical reactivity of the synthetic sample differed from those of natural protoaculeine B, which indicates the necessity for revision of the originally reported structure.

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Enantiospecific and diastereoselective synthesis of cis monobactams through electrophilic amination of chiral 3-hydroxyesters

Cited by 18 publications

References 74 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

Synthesis of 3-Amino-4-substituted Monocyclic ß-Lactams—Important Structural Motifs in Medicinal Chemistry

Total Synthesis of the Proposed Structure for Protoaculeine B, a Polycationic Marine Sponge Metabolite, with a Homogeneous Long-Chain Polyamine

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