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

RESUMEN

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.

MATERIALES

Referencia del producto

Marca

Descripción del producto

203939

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Palladium, powder, 99.995% trace metals basis

326666

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

686468

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

203998

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Palladium, powder or granules, 99.99% trace metals basis

267120

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267082

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464651

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348694

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348678

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

267112

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

348643

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

287474

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

GF39094904

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373206

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

GF19845120

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GF81435146

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

GF99541985

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

GF17478445

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

GF73152648

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

GF04041403

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

GF89451489

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

GF42154051

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

GF84888297

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

GF61398197

Palladium, wire reel, 0.05m, diameter 1.0mm, hard, 99.95%

GF50683631

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GF65598171

Palladium, wire reel, 0.2m, diameter 0.25mm, as drawn, 99.99+%

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Palladium, wire reel, 0.5m, diameter 0.25mm, hard, 99.95%

GF06612847

Palladium, foil, 0.1m coil, thickness 0.1mm, coil width 2mm, as rolled, 99.95%

GF03781863

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

GF90054659

Palladium, rod, 50mm, diameter 6.0mm, 99.95%