A stereoselective synthesis of 1,3,4-substituted β-lactams from polymer-supported chiral oxazolidine aldehyde

Gordon, Kirsteen; Bolger, M. V.; Khan, Nawaz; Balasubramanian, Shankar

doi:10.1016/s0040-4039(00)01516-1

Cited by 27 publications

(14 citation statements)

References 13 publications

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“…Having demonstrated the ability of CAN to cleave the p -benzyloxyphenyl group, the solid-phase synthesis of β-lactams was examined. Although a number of papers have described the solid-phase synthesis of these pharmacologically renowned compounds, − only one has offered a route to N-unsubstituted derivatives via the α-methyl-6-nitroveratrylamine photolabile linker . Resin 3 was therefore condensed with an excess of trans -hexenal in DCM with 4 Å molecular sieves for 0.5 h and was washed with anhydrous DCM.…”

mentioning

confidence: 99%

Exploring a Benzyloxyaniline Linker Utilizing Ceric Ammonium Nitrate (CAN) as a Cleavage Reagent: Solid-Phase Synthesis of N-Unsubstituted β-Lactams and Secondary Amides

Gordon

Balasubramanian

2000

Org. Lett.

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confidence: 99%

Exploring a Benzyloxyaniline Linker Utilizing Ceric Ammonium Nitrate (CAN) as a Cleavage Reagent: Solid-Phase Synthesis of N-Unsubstituted β-Lactams and Secondary Amides

Gordon

Balasubramanian

2000

Org. Lett.

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“…The use acetoxyketene [33] allows further modifications to give carbamate products. This chemistry has been extrapolated to the synthesis of enantiomerically enriched b-lactams starting from a polymer-bound version of Garners aldehyde [34]. A polymer-supported Mukaiyama-type reagent has been used for the preparation of b-lactams, using the Staudinger reaction.…”

Section: Biologically Relevant Monocyclic B-lactamsmentioning

confidence: 99%

The Chemistry of 2‐Azetidinones (β‐Lactams)

Alcaide¹,

Almendros²,

Luna³

2011

Modern Heterocyclic Chemistry

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The large number of recent reports on b-lactam chemistry demonstrates the increasing interest in this important class of compounds. Monocyclic b-lactams frequently serve as precursors for the synthesis of classical bicyclic b-lactam antibiotics. The cyclic 2-azetidinone skeleton has been extensively used as a template on which to build the heterocyclic structure fused to the four-membered ring, using the chirality and functionalization of the b-lactam nucleus as a stereocontrolling element. The discovery of nonclassical b-lactam antibiotics, such as monobactams and nocardicins, coupled with ever-growing new applications such as enzyme inhibition has triggered a renewed interest in the building of new monocyclic b-lactam derivatives. Besides the utility of b-lactams as biologically active agents, they are used as intermediates in a-and b-amino acid synthesis, as well as building blocks for alkaloids, heterocycles, taxoids and other types of compounds of biological and medicinal interest. Physicochemical Data Computational ChemistryTheoretical studies show that b-lactams are weaker bases, in the gas phase, than acyclic amides [1]. The attenuation of basicity upon cyclization is stronger than that found for cyclic ketones of similar size due to the existence of a negative hyperconjugation effect that is present in b-lactams but not in cyclic ketones. Ab initio calculations indicate that both b-lactams and acyclic amides are oxygen bases, but the gap between the oxygen and nitrogen intrinsic basicities is much smaller in the former due to the aforementioned cyclization effects. This decrease of the oxygen Modern Heterocyclic Chemistry, First Edition. Edited

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“…3). A polymer-supported synthesis of an array of a chirally pure b-lactams in high purity has been demonstrated [129] from a resin-bound chiral oxazolidine aldehyde. Application of resin-bound chiral oxazolidine aldehyde equivalent was explored for the synthesis of a small array of b-lactams.…”

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confidence: 99%

Recent Approaches Toward Solid Phase Synthesis of β-Lactams

Mandal

Ghosh

Basu

2010

Heterocyclic Scaffolds I

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Since the discovery of penicillin in 1929, b-lactam antibiotics have been recognized as potentially chemotherapeutic drugs of incomparable effectiveness, conjugating a broad spectrum of activity with very low toxicity. The primary motif azetidin-2-one ring (b-lactam) has been considered as specific pharmacophores and scaffolds. With the advent of combinatorial chemistry and automated parallel synthesis coupled with ample interests from the pharmaceutical industries, recent trends have been driven mostly by adopting solid phase techniques and polymersupported synthesis of b-lactams. The present survey will present an overview of the developments on the polymer-supported and solid phase techniques for the preparation of b-lactam ring or b-lactam containing antibiotics published over the last decade. Both unsubstituted and substitutions with different functional groups at various positions of b-lactams have been synthesized using solid phase technology. However, Wang resin and application of Staudinger [2+2] cycloaddition reaction have remained hitherto the major choice. It may be expected that other solid phase approaches involving different resins would be developed in the coming years.

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A stereoselective synthesis of 1,3,4-substituted β-lactams from polymer-supported chiral oxazolidine aldehyde

Cited by 27 publications

References 13 publications

Exploring a Benzyloxyaniline Linker Utilizing Ceric Ammonium Nitrate (CAN) as a Cleavage Reagent: Solid-Phase Synthesis of N-Unsubstituted β-Lactams and Secondary Amides

Exploring a Benzyloxyaniline Linker Utilizing Ceric Ammonium Nitrate (CAN) as a Cleavage Reagent: Solid-Phase Synthesis of N-Unsubstituted β-Lactams and Secondary Amides

The Chemistry of 2‐Azetidinones (β‐Lactams)

Recent Approaches Toward Solid Phase Synthesis of β-Lactams

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