Tetrahydroxanthones by sequential Pd-catalyzed C-O and C-C bond construction and use in the identification of the "antiausterity" pharmacophore of the kigamicins.

doi:10.1021/ol103103n

Paper

Tetrahydroxanthones by sequential Pd-catalyzed C-O and C-C bond construction and use in the identification of the "antiausterity" pharmacophore of the kigamicins.

Published Jan 26, 2011 · Penelope A. Turner, Ellanna M. Griffin, J. Whatmore

Organic letters

Q1 SJR score

36

Citations

0

Influential Citations

Full textSemantic Scholar

Abstract

Readily available C-acylated cycloalkanones undergo efficient Pd catalyzed ring closure/cross-coupling providing 7-substituted tetrahydroxanthones in a single operation. One of the synthesized derivatives (depicted) is shown to selectively kill pancreatic cancer (PANC-1) cells under conditions of nutrient deprivation indicating that the tetrahydroxanthone is responsible, in part, for the "antiausterity" effects of the naturally occurring kigamicins.

Study Snapshot

The synthesized derivative selectively kills pancreatic cancer cells under nutrient deprivation, suggesting it is responsible for the "antiausterity" effects of naturally occurring kigamicins.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Paper

Tetrahydroxanthones by sequential Pd-catalyzed C-O and C-C bond construction and use in the identification of the "antiausterity" pharmacophore of the kigamicins.

References

Citations

Visible-Light-Triggered Difluoroacetylation/Cyclization of Chromone-Tethered Alkenes Enabling Synthesis of Tetrahydroxanthones.

This study successfully synthesized various tetrahydroxanthone derivatives using readily available starting materials and photoredox conditions, offering a new approach for organic and biological chemistry.

Chemistry and biosynthesis of bacterial polycyclic xanthone natural products.

Bacterial polycyclic xanthone natural products (BPXNPs) show potential for treating diseases due to their potent activities and diverse structures, and recent progress in biosynthesis and chemical synthesis strategies show promise for their further development.

Flexible Approach for the Synthesis of Annulated 4H-Pyrans Based on a Cu(I)-Catalyzed C-Allylation/O-Vinylation Reaction of Cyclic 1-Bromoallyl Tosylates with Cyclic and Acyclic 1,3-Dicarbonyls.

This study presents a flexible approach for the synthesis of bisannulated 4H-pyrans using Cu(I)-catalyzed C-allylation/O-vinylation reactions of cyclic 1-bromoallyl tosylates with cyclic and acyclic 1,3

Access to Chiral Chromenones through Organocatalyzed Mannich/Annulation Sequence.

This study presents an efficient and practical method for accessing chiral chromenones with propargylamine or -amino ester moieties through organocatalyzed Mannich/Annulation sequence, yielding up to 98% ee.

An efficient approach for the synthesis of 1,2-dihydroxanthones enabled by one-pot Claisen condensation/cyclization reactions.

This study developed a mild, efficient, and green method for the synthesis of 1,2-dihydroxanthones in one pot using waste-induced relay catalysis, enabling their versatile conversion to xanthones and other complex structures.