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A Novel, Highly Selective, and General Methodology for the Synthesis of 1,5-Diene-Containing Oligoisoprenoids of All Possible Geometrical Combinations Exemplified by an Iterative and Convergent Synthesis of Coenzyme Q10

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journal contribution
posted on 04.01.2002 by Ei-ichi Negishi, Show-Yee Liou, Caiding Xu, Shouquan Huo
A truly general, versatile, and highly regio- and stereoselective methodology for the synthesis of terpenoids containing 1,5-diene units of E and/or Z geometry critically involves Pd-catalyzed homoallyl- and homopropargyl-alkenyl coupling and Zr-catalyzed carboalumination of alkynes. By using this methodology, coenzyme Q10, (E,Z,E)-geranylgeranoil, and other natural or unnatural compounds have been synthesized efficiently.