Biologically active γ-lactams: synthesis and natural sources

Caruano, Joséphine; Muccioli, Giulio G.; Robiette, Raphaël

doi:10.1039/c6ob01349j

Cited by 341 publications

(175 citation statements)

References 180 publications

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“…78 It has also been used as a building block for the synthesis of naturally occurring compounds. Lee and coworkers have reported the synthesis of (-)-8-episwainsonine 144 that is an indolizidine derivative from a commercially available 1-(R)-α-methylbenzylaziridine-2-methanol 141.…”

Section: Synthesis Of 2-pyrrolidinonesmentioning

confidence: 99%

Recent applications of aziridine ring expansion reactions in heterocyclic synthesis

Singh¹,

Sudheesh²,

Keroletswe³

2017

Arkivoc

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The inherent reactivity of the aziridine ring due to ring-strain makes it valuable building blocks for the synthesis of other heterocyclic motifs of biological relevance. Of particular significance is the generation of azomethine ylides from them and cycloaddition of ylides with alkenes, alkynes, and heterocumulenes. The ring undergoes opening followed by cyclization with a variety of reagents either in the presence of a catalyst or without any catalyst. This review article discusses the recent applications of aziridines in syntheses of four-to seven-membered heterocycles of biological relevance such as azetidines, 2

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Section: Synthesis Of 2-pyrrolidinonesmentioning

confidence: 99%

Recent applications of aziridine ring expansion reactions in heterocyclic synthesis

Singh¹,

Sudheesh²,

Keroletswe³

2017

Arkivoc

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“…The isoindolinone molecule consists of fused benzene and γ‐lactam rings (Scheme ). The five membered γ‐lactam ring contains the amide HN−C=O moiety, which is present in many important molecules . Isoindolinones also occur in nature; they are often bioactive and are widely used as building blocks in drug synthesis .…”

Section: Introductionmentioning

confidence: 99%

“…The five membered g-lactam ring contains the amide HNÀC=O moiety, which is present in many important molecules. [1] Isoindolinones also occur in nature; they are often bioactive and are widely used as building blocks in drug synthesis. [2] In particular, 3-substituted chiral isoindolinones are promising leads in pharmaceutical research.…”

Section: Introductionmentioning

confidence: 99%

The Vibrational Circular Dichroism Pattern of the ν(C=O) Bands in Isoindolinones

et al. 2018

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The IR and vibrational circular dichroism (VCD) spectra of both enantiomers of Me-, iPr-, nBu-, Ph-, and CH Ph-substituted isoindolinones in solution and KBr pellets were measured and interpreted by DFT calculations. The spectra in solution revealed no important differences in the C=O stretching vibration region while the interpretation of very distinct spectra taken in pellets required determining the crystal structures. The studied compounds crystallized in the P2 2 2 (Me, iPr, CH Ph), P3 (nBu), and P2 (Ph) space groups. We found that the quality of simulated spectra strongly depends on the substituent, the structure of the molecular cluster assumed, basis set, and use of the dispersion correction. The IR spectra can be reproduced well based on the simplest linear arrangement of hydrogen-bonded chains mimicking the molecular arrangement in the crystals. We found no common approach to reproduce all the registered VCD spectra in the crystal phase. For the Me and nBu isoindolinones, the VCD pattern was the best reproduced by full optimization of the selected large molecular clusters. For iPr, Ph and CH Ph derivatives optimizing only the position of H-atoms in a fragment frozen as in the crystal provides the best results. Such an approach can reduce the computation time from months to one week.

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“…γ‐Lactams are common motifs in bioactive natural products and pharmaceuticals . The cyclisation of acetamido metal carbenes A by reaction at N ‐tethered C−H or C−C bonds provides a powerful hydrocarbon‐forming strategy allowing access to different types of lactam (Scheme a) .…”

Section: Methodsmentioning

confidence: 99%

“…g-Lactamsa re common motifs in bioactive natural products and pharmaceuticals. [1] The cyclisation of acetamido metal carbenes A by reaction at N-tetheredC ÀHo rC ÀCb onds provides ap owerful hydrocarbon-forming strategy allowing access to different types of lactam (Scheme 1a). [2] Divergentp athways are often accessible in such processes and controlled by modi-fying the substrate structure,w ith a-proton, -methyl, or -electron-withdrawing groups commonly encountered,a nd by tuningt he reaction conditions and choice of catalyst.…”

mentioning

confidence: 99%

A Gold Carbene Manifold to Prepare Fused γ‐Lactams by Oxidative Cyclisation of Ynamides

Sánchez-Cantalejo

Priest

Davies

2018

Chemistry A European J

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Gold‐catalysed oxidative cyclisation reactions of ynamides offer great promise in γ‐lactam synthesis but are limited by preferential over‐oxidation to form α‐keto imides. Evaluating the factors that might limit N‐cyclisation pathways led to effective gold‐catalysed conditions that allow access to different fused γ‐lactams on changing the ynamide N‐substituent and accommodate previously incompatible substitution patterns. New and efficient methods for the synthesis of functionalised 3‐aryl indoles and cyclohepta[c]pyrrol‐1‐one derivatives are presented. These conditions illustrate the complementarity of gold catalysis to other metals.

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Biologically active γ-lactams: synthesis and natural sources

Cited by 341 publications

References 180 publications

Recent applications of aziridine ring expansion reactions in heterocyclic synthesis

Recent applications of aziridine ring expansion reactions in heterocyclic synthesis

The Vibrational Circular Dichroism Pattern of the ν(C=O) Bands in Isoindolinones

A Gold Carbene Manifold to Prepare Fused γ‐Lactams by Oxidative Cyclisation of Ynamides

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