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

61139

Sigma-Aldrich

Copper, turnings, purum p.a., ≥99.0%

31284

Sigma-Aldrich

Copper, electrolytic, Analytical Reagent, reag. Ph. Eur., ≥99.9% (complexometric), wire

12816

Sigma-Aldrich

Copper, foil, ≥99.8% (complexometric)

365327

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Copper, rod, diam. 11 mm, 99.9999% trace metals basis

266744

Sigma-Aldrich

Copper, foil, thickness 1.0 mm, 99.999% trace metals basis

254177

Sigma-Aldrich

Copper, beads, 2-8 mm, 99.9995% trace metals basis

326488

Sigma-Aldrich

Copper, beads, 2-8 mm, ≥99.99% trace metals basis

207780

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Copper, powder, <75 μm, 99%

GF16694006

Copper, rod, 50mm, diameter 6.35mm, as drawn, 99.999%

349216

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Copper, wire, diam. 1.0 mm, ≥99.9%

349151

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Copper, foil, thickness 0.5 mm, 99.98% trace metals basis

326429

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Copper, wire, diam. 0.25 mm, 99.999% trace metals basis

349224

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Copper, wire, diam. 2.0 mm, 99.999% trace metals basis

326410

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349208

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66955

Supelco

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IRMM522C

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203122

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BCR017B

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

767476

Sigma-Aldrich

Copper, sputtering target, diam. × thickness 2.00 in. × 0.25 in., 99.95% trace metals basis

774111

Sigma-Aldrich

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774103

Sigma-Aldrich

Copper, nanopowder, 60-80 nm particle size (SAXS), ≥99.5% trace metals basis

GF98066054

Copper, wire reel, 100m, diameter 0.5mm, annealed, 99.9%

223409

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520381

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349178

Sigma-Aldrich

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326445

Sigma-Aldrich

Copper, bars (random sizes), ≥99.999% trace metals basis

266086

Sigma-Aldrich

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326453

Sigma-Aldrich

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