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

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

Palladium, powder or granules, 99.99% trace metals basis

Sigma-Aldrich

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

Sigma-Aldrich

Palladium, sponge, 99.9% trace metals basis

Sigma-Aldrich

Palladium, powder, 99.995% trace metals basis

Palladium, foil, 15mm disks, thickness 0.006mm, 99.95%

Palladium, foil, 50x50mm, thickness 0.1mm, as rolled, 99.99+%

Palladium, foil, 8mm disks, thickness 0.0125mm, 99.95%

Palladium, foil, 1m coil, thickness 0.1mm, coil width 2mm, as rolled, 99.95%

Palladium, foil, 4mm disks, thickness 0.025mm, as rolled, 99.95%

Palladium, foil, 15mm disks, thickness 0.008mm, 99.95%

Palladium, foil, 50x50mm, thickness 0.25mm, as rolled, 99.95%

Palladium, foil, 10mm disks, thickness 0.006mm, 99.95%

Palladium, foil, 15mm disks, thickness 0.125mm, as rolled, 99.95%

Palladium, foil, 100x100mm, thickness 0.1mm, as rolled, 99.95%

Palladium, foil, 8mm disks, thickness 0.025mm, as rolled, 99.95%

Palladium, foil, 6mm disks, thickness 0.006mm, 99.95%

Palladium, foil, 6mm disks, thickness 0.025mm, as rolled, 99.95%

Palladium, foil, 10mm disks, thickness 0.02mm, as rolled, 99.95%

Palladium, foil, 4mm disks, thickness 0.025mm, as rolled, 99.99+%

Palladium, foil, 6mm disks, thickness 0.25mm, as rolled, 99.95%

Palladium, foil, 50x50mm, thickness 0.25mm, as rolled, 99.99+%