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

ABSTRAKT

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.

MATERIAŁY

Numer produktu

Marka

Opis produktu

266086

Sigma-Aldrich

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

357456

Sigma-Aldrich

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

349178

Sigma-Aldrich

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

311405

Sigma-Aldrich

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

223409

Sigma-Aldrich

Copper, shot, −3-+14 mesh, 99%

203122

Sigma-Aldrich

Copper, powder, 99.99% trace metals basis

326453

Sigma-Aldrich

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

IRMM522A

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

BCR017B

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

IRMM522C

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

BCR054R

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

GF16408425

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

GF76135631

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

GF29372441

Copper, sphere, 100pcs, diameter 1.0mm, precision sphere grade 200

GF41333273

Copper, tube, 100mm, outside diameter 1.5mm, inside diameter 0.6mm, wall thickness 0.45mm, as drawn, 99.9%

GF51455459

Copper, tube, 1000mm, outside diameter 3.0mm, inside diameter 1.2mm, wall thickness 0.9mm, as drawn, 99.9%

GF83058633

Copper, tube, 100mm, outside diameter 0.95mm, inside diameter 0.29mm, wall thickness 0.33mm, as drawn, 99.9%

GF19533090

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

GF88932066

Copper, rod, 500mm, diameter 9.5mm, hard, 99.9%

GF95287966

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

GF84281935

Copper, tube, 100mm, outside diameter 0.25mm, inside diameter 0.05mm, wall thickness 0.1mm, as drawn, 99.9%

GF14973060

Copper, tube, 100mm, outside diameter 10.4mm, inside diameter 10mm, wall thickness 0.2mm, 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+%

GF54651146

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

GF22027799

Copper, tube, 1000mm, outside diameter 6.35mm, inside diameter 4.93mm, wall thickness 0.71mm, as drawn, 99.9%

GF52726608

Copper - O.F.H.C., foil, 150x150mm, thickness 0.1mm, hard, 99.95+%

GF81522446

Copper - O.F.H.C., foil, 25x25mm, thickness 0.25mm, half hard, 99.95+%

GF88173647

Copper - O.F.H.C., foil, 100x100mm, thickness 0.25mm, half hard, 99.95+%

GF64598237

Copper - O.F.H.C., foil, 300x300mm, thickness 0.5mm, half hard, 99.95+%