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

ABSTRACT

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.

MATERIALS

Product Number

Brand

Product Description

686468

Sigma-Aldrich

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

373206

Sigma-Aldrich

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

348694

Sigma-Aldrich

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

348643

Sigma-Aldrich

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

267082

Sigma-Aldrich

Palladium, sponge, 99.9% trace metals basis

326666

Sigma-Aldrich

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

287474

Sigma-Aldrich

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

464651

Sigma-Aldrich

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

203939

Sigma-Aldrich

Palladium, powder, 99.995% trace metals basis

267120

Sigma-Aldrich

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

267112

Sigma-Aldrich

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

203998

Sigma-Aldrich

Palladium, powder or granules, 99.99% trace metals basis

348678

Sigma-Aldrich

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

GF74894136

Palladium, foil, 8mm disks, thickness 0.25mm, as rolled, 99.95%

GF44874995

Palladium, foil, light tested, 100x100mm, thickness 0.047mm, as rolled, 99.95%

GF60084424

Palladium, foil, light tested, 100x100mm, thickness 0.025mm, as rolled, 99.99+%

GF94632576

Palladium, foil, light tested, 100x100mm, thickness 0.075mm, as rolled, 99.95%

GF90427866

Palladium, foil, light tested, 100x100mm, thickness 0.025mm, as rolled, 99.95%

GF23374661

Palladium, foil, 8mm disks, thickness 0.50mm, as rolled, 99.95%

GF60234533

Palladium, foil, 8mm disks, thickness 0.25mm, as rolled, 99.99+%

GF22660264

Palladium, wire reel, 0.1m, diameter 0.5mm, as drawn, 99.95%

GF02178761

Palladium, wire reel, 2m, diameter 0.025mm, as drawn, 99.9%

GF19701503

Palladium, wire reel, 0.5m, diameter 0.125mm, hard, 99.95%

GF51724784

Palladium, wire reel, 0.1m, diameter 0.25mm, as drawn, 99.99+%

GF05176122

Palladium, wire reel, 5m, diameter 0.05mm, as drawn, 99.9%

GF12546581

Palladium, wire reel, 0.1m, diameter 0.25mm, hard, 99.95%

GF24288790

Palladium, wire reel, 5m, diameter 0.25mm, hard, 99.95%

GF88744843

Palladium, wire reel, 1m, diameter 0.02mm, as drawn, 99.95%

GF99771261

Palladium, wire reel, 0.5m, diameter 0.25mm, as drawn, 99.99+%

GF93105547

Palladium, wire reel, 2m, diameter 0.02mm, as drawn, 99.95%