Impact of copper-catalyzed cross-coupling reactions in natural product synthesis: the emergence of new retrosynthetic paradigms.

Impact of copper-catalyzed cross-coupling reactions in natural product synthesis: the emergence of new retrosynthetic paradigms.

Natural product reports (2013-10-25)

Gwilherm Evano, Cédric Theunissen, Alexandre Pradal

ABSTRACT

Copper-catalyzed Ullmann-Goldberg-type cross-coupling reactions have undergone nothing short of a renaissance over the last decade and an impressive number of procedures are now available for the formation of C-N, C-O and C-S bonds with remarkable efficiencies and surgical precision. These reactions have been recently integrated into natural product synthesis, which clearly resulted in the emergence of new retrosynthetic paradigms and bond disconnections. The impact of copper-catalyzed cross-coupling reactions in natural product synthesis will be overviewed in this article with an emphasis on the evolution of strategies due to copper catalysis, mostly by comparison with alternative tactics and their relative efficiencies.

MATERIALS

Product Number

Brand

Product Description

BCR017B

Copper (S, P), BCR^®, certified reference material, chips

223409

Sigma-Aldrich

Copper, shot, −3-+14 mesh, 99%

349178

Sigma-Aldrich

Copper, foil, thickness 0.25 mm, 99.98% trace metals basis

266086

Sigma-Aldrich

Copper, powder, <425 μm, 99.5% trace metals basis

BCR054R

Copper (O), BCR^®, certified reference material, rod

326453

Sigma-Aldrich

Copper, powder (spheroidal), 10-25 μm, 98%

311405

Sigma-Aldrich

Copper, ACS reagent, granular, 10-40 mesh, ≥99.90%

357456

Sigma-Aldrich

Copper, powder (dendritic), <45 μm, 99.7% trace metals basis

203122

Sigma-Aldrich

Copper, powder, 99.999% trace metals basis

IRMM522C

Copper, IRMM^®, certified reference material, 0.5 mm wire

IRMM522A

Copper, IRMM^®, certified reference material, 0.1 mm foil

GF52942226

Copper, tube, 100mm, outside diameter 0.65mm, inside diameter 0.21mm, wall thickness 0.22mm, as drawn, 99.9%

GF42838162

Copper, tube, 100mm, outside diameter 6.0mm, inside diameter 4mm, wall thickness 1.0mm, as drawn, 99.9%

GF31266121

Copper, tube, 200mm, outside diameter 1.5mm, inside diameter 0.6mm, wall thickness 0.45mm, as drawn, 99.9%

GF52673250

Copper, tube, 200mm, outside diameter 1.75mm, inside diameter 0.33mm, wall thickness 0.71mm, as drawn, 99.9%

GF35241892

Copper, tube, 200mm, outside diameter 0.25mm, inside diameter 0.05mm, wall thickness 0.1mm, as drawn, 99.9%

GF73652250

Copper, tube, 500mm, outside diameter 1.5mm, inside diameter 0.6mm, wall thickness 0.45mm, as drawn, 99.9%

GF35866761

Copper, tube, 200mm, outside diameter 10.4mm, inside diameter 10mm, wall thickness 0.2mm, as drawn, 99.9%

GF37574523

Copper, tube, 200mm, outside diameter 6.35mm, inside diameter 4.93mm, wall thickness 0.71mm, as drawn, 99.9%

GF64429016

Copper, tube, 100mm, outside diameter 2.5mm, inside diameter 1.9mm, wall thickness 0.3mm, as drawn, 99.9%

GF95287966

Copper, tube, 1000mm, outside diameter 3.5mm, inside diameter 1.56mm, wall thickness 0.97mm, as drawn, 99.9%

GF14973060

Copper, tube, 100mm, outside diameter 10.4mm, inside diameter 10mm, wall thickness 0.2mm, as drawn, 99.9%

GF63476792

Copper, rod, 100mm, diameter 9.5mm, as drawn, 99.99+%

GF03497957

Copper, tube, 1000mm, outside diameter 4.0mm, inside diameter 3.2mm, wall thickness 0.4mm, as drawn, 99.9%

GF54025792

Copper, tube, 100mm, outside diameter 1.2mm, inside diameter 0.56mm, wall thickness 0.32mm, as drawn, 99.9%

GF31651455

Copper, rod, 50mm, diameter 16mm, as drawn, 99.99+%

GF16408425

Copper, tube, 1000mm, outside diameter 2.5mm, inside diameter 1.9mm, wall thickness 0.3mm, as drawn, 99.9%

GF19533090

Copper, tube, 1000mm, outside diameter 1.75mm, inside diameter 0.33mm, wall thickness 0.71mm, as drawn, 99.9%

GF76135631

Copper, rod, 50mm, diameter 5.0mm, as drawn, 99.999%

GF54651146

Copper, tube, 1000mm, outside diameter 0.25mm, inside diameter 0.05mm, wall thickness 0.1mm, as drawn, 99.9%