Skip to Content

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

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

Palladium, powder, 99.995% trace metals basis

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

Palladium, sponge, 99.9% trace metals basis

Sigma-Aldrich

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Palladium, wire reel, 2m, diameter 0.25mm, hard, 99.95%

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

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

Palladium, wire reel, 0.1m, diameter 0.125mm, hard, 99.95%

Palladium, tube, 50mm, outside diameter 2.0mm, inside diameter 1.6mm, wall thickness 0.2mm, as drawn, 99.95%

Palladium, wire reel, 0.1m, diameter 1.0mm, hard, 99.95%

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

Palladium, wire reel, 1m, diameter 0.125mm, hard, 99.95%