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  • 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, evaporation slug, diam. × L 0.6 cm × 0.6 cm, 99.95% trace metals basis
Sigma-Aldrich
Palladium, wire, diam. 0.5 mm, 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 or granules, 99.99% trace metals basis
Sigma-Aldrich
Palladium, powder, 99.995% trace metals basis
Sigma-Aldrich
Palladium, sponge, 99.9% 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, 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, powder, <1 μm, ≥99.9% trace metals basis
Palladium, foil, not light tested, 100x100mm, thickness 0.025mm, as rolled, 99.99+%
Palladium, foil, not light tested, 25x25mm, thickness 0.006mm, 99.95%
Palladium, foil, not light tested, 25x25mm, thickness 0.025mm, as rolled, 99.99+%
Palladium, foil, not light tested, 25x25mm, thickness 0.00075mm, permanent polyester support, 99.75%
Palladium, foil, 8mm disks, thickness 0.006mm, 99.95%
Palladium, foil, 8mm disks, thickness 0.025mm, as rolled, 99.95%
Palladium, foil, not light tested, 100x100mm, thickness 0.006mm, 99.95%
Palladium, wire reel, 2m, diameter 0.25mm, hard, 99.95%
Palladium, microfoil, disks, 25mm, thinness 0.5μm, specific density 303.4μg/cm2, permanent mylar 3.5μm support, 99.99%
Palladium, wire reel, 1m, diameter 0.125mm, hard, 99.95%
Palladium, rod, 50mm, diameter 2.0mm, 99.95%
Palladium, wire reel, 2m, diameter 0.25mm, as drawn, 99.99+%
Palladium, wire reel, 0.5m, diameter 1.0mm, hard, 99.95%
Palladium, microfoil, disks, 50mm, thinness 0.05μm, specific density 63.6μg/cm2, permanent mylar 3.5μm support, 99.99%
Palladium, microfoil, disks, 10mm, thinness 0.1μm, specific density 119.2μg/cm2, permanent mylar 3.5μm support, 99.99%
Palladium, wire reel, 5m, diameter 0.05mm, as drawn, 99.9%
Palladium, wire reel, 2m, diameter 0.02mm, as drawn, 99.95%