Late-Stage Functionalization of Biologically Active Heterocycles Through Photoredox Catalysis

2014 ◽  
Vol 126 (19) ◽  
pp. 4902-4906 ◽  
Author(s):  
Daniel A. DiRocco ◽  
Kevin Dykstra ◽  
Shane Krska ◽  
Petr Vachal ◽  
Donald V. Conway ◽  
...  
Keyword(s):  
Late Stage ◽  
Biologically Active ◽  
Photoredox Catalysis

Late-Stage Functionalization of Biologically Active Heterocycles Through Photoredox Catalysis

2014 ◽  
Vol 53 (19) ◽  
pp. 4802-4806 ◽  
Author(s):  
Daniel A. DiRocco ◽  
Kevin Dykstra ◽  
Shane Krska ◽  
Petr Vachal ◽  
Donald V. Conway ◽  
...  
Keyword(s):  
Late Stage ◽  
Biologically Active ◽  
Photoredox Catalysis

scholarly journals Combined Photoredox and Carbene Catalysis for the Synthesis of Ketones from Carboxylic Acids

2020 ◽  
Author(s):  
Anna Davies ◽  
keegan fitzpatrick ◽  
Rick Betori ◽  
Karl Scheidt
Keyword(s):  
Carboxylic Acids ◽  
Late Stage ◽  
Pharmaceutical Compounds ◽  
Single Electron ◽  
Photoredox Catalysis ◽  
Radical Coupling ◽  
Electron Reduction

Disclosed herein is the development of a novel single-electron reduction of acyl azoliums for the formation of ketones from carboxylic acids. Facile construction of the acyl azolium <i>in situ</i> followed by a radical-radical coupling was made possible using merged NHC-photoredox catalysis. The utility of this protocol in synthesis was demonstrated in the late-stage functionalization of a variety of pharmaceutical compounds.

scholarly journals Modular synthesis of α-fluorinated arylmethanes via desulfonylative cross-coupling

2019 ◽  
Vol 10 (1) ◽  
Author(s):  
Masakazu Nambo ◽  
Jacky C.-H. Yim ◽  
Luiza B. O. Freitas ◽  
Yasuyo Tahara ◽  
Zachary T. Ariki ◽  
...  
Keyword(s):  
Biological Activity ◽  
Late Stage ◽  
Recent Progress ◽  
Cross Coupling ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Active Compounds ◽  
Arylboronic Acids ◽  
Modular Synthesis ◽  
Synthetic Routes

Abstract α-Fluoromethylarenes are common substructures in pharmaceuticals and agrochemicals, with the introduction of fluorine often resulting in improved biological activity and stability. Despite recent progress, synthetic routes to α-fluorinated diarylmethanes are still rare. Herein we describe the Pd-catalyzed Suzuki-Miyaura cross-coupling of α-fluorinated benzylic triflones with arylboronic acids affording structurally diverse α-fluorinated diarylmethanes. The ease of synthesis of fluorinated triflones as the key starting materials enables powerful late-stage transformations of known biologically active compounds into fluorinated analogs.

Synthetic approaches to [5,6]-benzannulated spiroketal natural products

2011 ◽  
Vol 84 (6) ◽  
pp. 1379-1390 ◽  
Author(s):  
Michael C. McLeod ◽  
Margaret A. Brimble ◽  
Dominea C. K. Rathwell ◽  
Zoe E. Wilson ◽  
Tsz-Ying Yuen
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Electronic Properties ◽  
Late Stage ◽  
Biologically Active ◽  
Formal Synthesis ◽  
Berkelic Acid ◽  
Synthetic Approaches

Studies toward the synthesis of three biologically active [5,6]-benzannulated spiroketal natural products are described. The first total synthesis of paecilospirone is reported, employing a late-stage, pH-neutral spiroketalization. A formal synthesis of γ-rubromycin is described, where the spiroketal moiety is formed by delicate manipulation of the electronic properties of the spirocyclization precursor. Finally, model work toward the total synthesis of berkelic acid is summarized, introducing a novel Horner–Wadsworth–Emmons/oxa-Michael (HWE/oxa-M) cascade to access the spiroketal precursor.

scholarly journals Late-Stage Diversification of Biologically Active Molecules via Chemoenzymatic C–H Functionalization

ACS Catalysis ◽  
2016 ◽  
Vol 6 (3) ◽  
pp. 1451-1454 ◽  
Author(s):  
Landon J. Durak ◽  
James T. Payne ◽  
Jared C. Lewis
Keyword(s):  
Late Stage ◽  
Biologically Active

scholarly journals Photooxygenation of an amino-thienopyridone yields a more potent PTP4A3 inhibitor

2016 ◽  
Vol 14 (27) ◽  
pp. 6398-6402 ◽  
Author(s):  
Joseph M. Salamoun ◽  
Kelley E. McQueeney ◽  
Kalyani Patil ◽  
Steven J. Geib ◽  
Elizabeth R. Sharlow ◽  
...  
Keyword(s):  
Late Stage ◽  
Biologically Active

Late-stage photooxygenation can generate novel biologically active lead structures.

Late-stage diversification of biologically active pyridazinones via a direct C–H functionalization strategy

2015 ◽  
Vol 13 (2) ◽  
pp. 539-548 ◽  
Author(s):  
Wei Li ◽  
Zhoulong Fan ◽  
Kaijun Geng ◽  
Youjun Xu ◽  
Ao Zhang
Keyword(s):  
Late Stage ◽  
Biologically Active ◽  
Directing Group

Divergent ortho-selective C–H functionalization was successfully established using a pyridazinone moiety as an internal directing group.

scholarly journals Late stage iodination of biologically active agents using a one-pot process from aryl amines

RSC Advances ◽  
2017 ◽  
Vol 7 (86) ◽  
pp. 54881-54891 ◽  
Author(s):  
Nikki L. Sloan ◽  
Sajinder K. Luthra ◽  
Graeme McRobbie ◽  
Sally L. Pimlott ◽  
Andrew Sutherland
Keyword(s):  
Late Stage ◽  
Biologically Active ◽  
One Pot ◽  
Aryl Iodide ◽  
Aryl Amines ◽  
Tandem Process

A tandem process has been developed for the general preparation of aryl iodide compounds from anilines that is also applicable for the late-stage iodination of biologically active agents.

Sign in / Sign up

Export Citation Format

Share Document