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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, powder, <1 μm, ≥99.9% trace metals basis
Sigma-Aldrich
Palladium, powder, 99.995% trace metals basis
Sigma-Aldrich
Palladium black, surface area 40-60 m2/g, 99.95% trace metals basis
Sigma-Aldrich
Palladium, granular, 99.99% trace metals basis
Sigma-Aldrich
Palladium, wire, diam. 0.5 mm, 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, sponge, 99.9% trace metals basis
Sigma-Aldrich
Palladium, foil, thickness 0.5 mm, 99.9% trace metals basis
Sigma-Aldrich
Palladium, foil, thickness 0.05 mm, 99.9% trace metals basis
Palladium, foil, 50x50mm, thickness 0.1mm, as rolled, 99.95%
Palladium, foil, 50x50mm, thickness 0.25mm, as rolled, 99.95%
Palladium, foil, light tested, 25x25mm, thickness 0.006mm, 99.95%
Palladium, foil, light tested, 25x25mm, thickness 0.025mm, as rolled, 99.95%
Palladium, foil, light tested, 25x25mm, thickness 0.025mm, as rolled, 99.99+%
Palladium, foil, light tested, 25x25mm, thickness 0.03mm, as rolled, 99.95%
Palladium, foil, light tested, 25x25mm, thickness 0.047mm, as rolled, 99.95%
Palladium, foil, light tested, 25x25mm, thickness 0.075mm, as rolled, 99.95%
Palladium, foil, light tested, 50x50mm, thickness 0.025mm, as rolled, 99.99+%
Palladium, foil, light tested, 50x50mm, thickness 0.03mm, as rolled, 99.95%
Palladium, foil, light tested, 50x50mm, thickness 0.047mm, as rolled, 99.95%
Palladium, foil, light tested, 50x50mm, thickness 0.075mm, as rolled, 99.95%
Palladium, foil, not light tested, 100x100mm, thickness 0.004mm, 99.95%
Palladium, foil, not light tested, 100x100mm, thickness 0.005mm, 99.95%
Palladium, foil, not light tested, 100x100mm, thickness 0.006mm, 99.95%
Palladium, foil, not light tested, 100x100mm, thickness 0.008mm, 99.95%
Palladium, foil, not light tested, 100x100mm, thickness 0.0125mm, 99.95%
Palladium, foil, not light tested, 100x100mm, thickness 0.025mm, as rolled, 99.95%
Palladium, foil, not light tested, 100x100mm, thickness 0.02mm, as rolled, 99.95%
Palladium, foil, not light tested, 100x100mm, thickness 0.03mm, as rolled, 99.95%