Development of a second generation palladium-catalyzed cycloalkenylation and its application to bioactive natural product synthesis.

Development of a second generation palladium-catalyzed cycloalkenylation and its application to bioactive natural product synthesis.

Natural product communications (2013-08-29)

Masahiro Toyota

RÉSUMÉ

A novel palladium-catalyzed intramolecular oxidative alkylation of unactivated olefins is described. This protocol was devised to solve one of the drawbacks of the original palladium-catalyzed cycloalkenylation that we developed. We call this new procedure the 'second generation palladium-catalyzed cycloalkenylation'. This protocol has been applied to the total syntheses of cis-195A, trans-195A, boonein, scholareins A, C, D, and alpha-skytanthine.

MATÉRIAUX

Référence du produit

Marque

Description du produit

203939

Sigma-Aldrich

Palladium, powder, 99.995% trace metals basis

326666

Sigma-Aldrich

Palladium, powder, <1 μm, ≥99.9% trace metals basis

203998

Sigma-Aldrich

Palladium, powder or granules, 99.99% trace metals basis

686468

Sigma-Aldrich

Palladium, nanopowder, <25 nm particle size (TEM), ≥99.5%

267120

Sigma-Aldrich

Palladium, foil, thickness 0.025 mm, 99.9% trace metals basis

464651

Sigma-Aldrich

Palladium, powder, <75 μm, 99.9% trace metals basis

267082

Sigma-Aldrich

Palladium, sponge, 99.9% trace metals basis

348694

Sigma-Aldrich

Palladium, wire, diam. 0.5 mm, 99.9% trace metals basis

348678

Sigma-Aldrich

Palladium, foil, thickness 1.0 mm, 99.9% trace metals basis

267112

Sigma-Aldrich

Palladium, wire, diam. 1.0 mm, 99.9% trace metals basis

287474

Sigma-Aldrich

Palladium, foil, thickness 0.5 mm, 99.9% trace metals basis

348643

Sigma-Aldrich

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

GF39094904

Palladium, tube, 50mm, outside diameter 1.0mm, inside diameter 0.8mm, wall thickness 0.1mm, as drawn, 99.95%

373206

Sigma-Aldrich

Palladium, evaporation slug, diam. × L 0.6 cm × 0.6 cm, 99.95% trace metals basis

GF81435146

Palladium, rod, 100mm, diameter 2.0mm, 99.95%

GF19845120

Palladium, rod, 50mm, diameter 4.0mm, 99.95%

GF73152648

Palladium, rod, 10mm, diameter 6.0mm, 99.95%

GF35373551

Palladium, foil, 10x10mm, thickness 0.50mm, as rolled, 99.99+%

GF17478445

Palladium, foil, 25x25mm, thickness 0.50mm, as rolled, 99.99+%

GF89451489

Palladium, rod, 50mm, diameter 2.0mm, 99.95%

GF04041403

Palladium, wire reel, 1m, diameter 0.05mm, as drawn, 99.9%

GF99541985

Palladium, tube, 200mm, outside diameter 2.0mm, inside diameter 1.6mm, wall thickness 0.2mm, as drawn, 99.95%

GF68272588

Palladium, rod, 25mm, diameter 6.0mm, 99.95%

GF03781863

Palladium, foil, light tested, 25x25mm, thickness 0.025mm, as rolled, 99.95%

GF84888297

Palladium, microfoil, disks, 25mm, thinness 0.25μm, specific density 303.4μg/cm², permanent mylar 3.5μm support, 99.99%

GF35196330

Palladium, tube, 100mm, outside diameter 2.0mm, inside diameter 1.6mm, wall thickness 0.2mm, as drawn, 99.95%

GF71407650

Palladium, wire reel, 1m, diameter 0.25mm, as drawn, 99.99+%

GF93848260

Palladium, foil, 25x25mm, thickness 0.25mm, as rolled, 99.99+%

GF42154051

Palladium, foil, light tested, 50x50mm, thickness 0.025mm, as rolled, 99.99+%

GF88212898

Palladium, foil, not light tested, 50x50mm, thickness 0.025mm, as rolled, 99.95%