Palladium-catalyzed 1,4-difunctionalization of butadiene to form skipped polyenes.

doi:10.1021/ja3110544

Paper

Palladium-catalyzed 1,4-difunctionalization of butadiene to form skipped polyenes.

Published Mar 12, 2013 · M. McCammant, L. Liao, M. Sigman

Journal of the American Chemical Society

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113

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0

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Abstract

A palladium-catalyzed 1,4-addition across the commodity chemical 1,3-butadiene to afford skipped polyene products is reported. Through a palladium σ → π → σ allyl isomerization, two new carbon-carbon bonds are formed with high regioselectivity and trans stereoselectivity of the newly formed alkene. The utility of this method is highlighted by the successful synthesis of the ripostatin A skipped triene core.

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Study Snapshot

This study demonstrates a palladium-catalyzed 1,4-addition across 1,3-butadiene to form skipped polyenes, which can be used to synthesize ripostatin A's skipped triene core.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Palladium-catalyzed 1,4-difunctionalization of butadiene to form skipped polyenes.

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