Enantioselective Synthesis of Alkaloids from Phenylglycinol-Derived Lactams

Amat, Mercedes; Llor, Núria; Griera, Rosa; Pérez, Maria; Bosch, Joan

doi:10.1177/1934578x1100600412

Cited by 5 publications

(1 citation statement)

References 32 publications

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“…Meyers’ lactamization reaction has been widely used for the stereoselective synthesis of bicyclic lactams, which may be utilized as chiral building blocks for the stereoselective construction of five- and six-membered nitrogen-containing heterocycles [ 27 , 28 ]. It is a well-known tool for the synthesis of natural products (especially alkaloids) from phenylglycinol-derived bi- and tricyclic lactams [ 29 , 30 , 31 ]. However, to the best of our knowledge, this methodology has not been extended to derive 4-piperidone δ–keto-ester until the work of our group [ 32 ].…”

Section: Resultsmentioning

confidence: 99%

Rapid and Efficient Access to Novel Bio-Inspired 3-Dimensional Tricyclic SpiroLactams as Privileged Structures via Meyers’ Lactamization

et al. 2023

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The concept of privileged structure has been used as a fruitful approach for the discovery of novel biologically active molecules. A privileged structure is defined as a semi-rigid scaffold able to display substituents in multiple spatial directions and capable of providing potent and selective ligands for different biological targets through the modification of those substituents. On average, these backbones tend to exhibit improved drug-like properties and therefore represent attractive starting points for hit-to-lead optimization programs. This article promotes the rapid, reliable, and efficient synthesis of novel, highly 3-dimensional, and easily functionalized bio-inspired tricyclic spirolactams, as well as an analysis of their drug-like properties.

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Section: Resultsmentioning

confidence: 99%

Rapid and Efficient Access to Novel Bio-Inspired 3-Dimensional Tricyclic SpiroLactams as Privileged Structures via Meyers’ Lactamization

et al. 2023

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ChemInform Abstract: Enantioselective Synthesis of Alkaloids from Phenylglycinol‐Derived Lactams

Amat¹,

Llor²,

Griera³

et al. 2011

ChemInform

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Enantiodivergent Approach to the Synthesis of Cis-2,6-Disubstituted Piperidin-4-ones

2019

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Enantiopure β-amino ketone derivatives were synthesized by decarboxylative Mannich reaction of chiral N-tert-butanesulfinyl imines with β-keto acids, and were subsequently transformed into cis-2,6-disubstituted piperidin-4-ones through an organocatalyzed condensation with aldehydes. Both enantiomers were accessible from the same precursors by inverting the order in the reaction sequence of the aldehydes involved in the imine formation and the intramolecular Mannich condensation. The synthesis of the piperidine alkaloids (+)-241D, (−)-epimyrtine and (−)lasubine II demonstrated the utility of this methodology.

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Enantioselective Synthesis of Alkaloids from Phenylglycinol-Derived Lactams

Cited by 5 publications

References 32 publications

Rapid and Efficient Access to Novel Bio-Inspired 3-Dimensional Tricyclic SpiroLactams as Privileged Structures via Meyers’ Lactamization

Rapid and Efficient Access to Novel Bio-Inspired 3-Dimensional Tricyclic SpiroLactams as Privileged Structures via Meyers’ Lactamization

ChemInform Abstract: Enantioselective Synthesis of Alkaloids from Phenylglycinol‐Derived Lactams

Enantiodivergent Approach to the Synthesis of Cis-2,6-Disubstituted Piperidin-4-ones

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