Neopyrrolomycins with Broad Spectrum Antibacterial Activity

Hopp, D. Craig; Rhea, Joshua; Jacobsen, Daniel E.; Romari, Khadidja; Smith, Chris; Rabenstein, John; Irigoyen, Macarena; Clarke, Midori; Francis, Linda; Luche, Michele; Carr, Grant; Mocek, Ursula

doi:10.1021/np800632f

Cited by 9 publications

(2 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…As part of our ongoing research efforts, we recently became interested in atroposelectively constructing an axially chiral axis between a five-membered heterocycle and an aryl ring 17 , since these molecules are valuable, yet their asymmetric synthesis is inherently challenging and has not been well studied 18 , 19 . In this context, N -arylpyrrole skeletons are often found in natural products, chiral ligands, and catalysts 20 – 25 (Fig. 1a ), therefore, catalytic asymmetric synthetic methods to access this type of molecules would be of great significance and highly appealing.…”

Section: Introductionmentioning

confidence: 99%

Diastereo- and atroposelective synthesis of N-arylpyrroles enabled by light-induced phosphoric acid catalysis

Dai,

Zhou,

Guo

et al. 2023

Nat Commun

View full text Add to dashboard Cite

The C−N axially chiral N-arylpyrrole motifs are privileged scaffolds in numerous biologically active molecules and natural products, as well as in chiral ligands/catalysts. Asymmetric synthesis of N-arylpyrroles, however, is still challenging, and the simultaneous creation of contiguous C−N axial and central chirality remains unknown. Herein, a diastereo- and atroposelective synthesis of N-arylpyrroles enabled by light-induced phosphoric acid catalysis has been developed. The key transformation is a one-pot, three-component oxo-diarylation reaction, which simultaneously creates a C−N axial chirality and a central quaternary stereogenic center. A broad range of unactivated alkynes were readily employed as a reaction partner in this transformation, and the N-arylpyrrole products are obtained in good yields, with excellent enantioselectivities and very good diastereoselectivities. Notably, the N-arylpyrrole skeletons represent interesting structural motifs that could be used as chiral ligands and catalysts in asymmetric catalysis.

show abstract

Section: Introductionmentioning

confidence: 99%

Diastereo- and atroposelective synthesis of N-arylpyrroles enabled by light-induced phosphoric acid catalysis

Dai,

Zhou,

Guo

et al. 2023

Nat Commun

View full text Add to dashboard Cite

show abstract

“…Neopyrrolomycins isolated from Streptomyces sp. MI424–38F1 exhibit broad spectrum antibacterial activity . Furthermore, due to their specific electronic properties among biaryls, chiral N-arylpyrroles have been used as chiral organocatalysts and ligands in enantioselective reactions (Figure ).…”

mentioning

confidence: 99%

A Central-to-Axial Chirality Conversion Strategy for the Synthesis of C–N Axially Chiral N-Arylpyrroles

et al. 2022

View full text Add to dashboard Cite

We present a central-to-axial chirality conversion strategy for the construction of C−N axially chiral N-arylpyrroles via a gold(I)-catalyzed 5-endo-dig cyclization/dehydration cascade from amino acid derivatives. The reaction exhibits high efficiency on the central-to-axial chirality conversion. Density functional theory calculations suggest that the stereospecificity during the central-to-axial chirality conversion lies in the stability of the conformations of the amino alcohol and the corresponding low barrier transition state.

show abstract