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Ethynylation of Aryl Halides by a Modified Suzuki Reaction: Application to the Syntheses of Combretastatin A-4, A-5 and Lunularic Acid

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Fürstner,  Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Nikolakis,  Katharina
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Fürstner, A., & Nikolakis, K. (1996). Ethynylation of Aryl Halides by a Modified Suzuki Reaction: Application to the Syntheses of Combretastatin A-4, A-5 and Lunularic Acid. Liebigs Annalen, (12), 2107-2113. doi:10.1002/jlac.199619961224.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0024-07A4-1
Abstract
On treatment with trimethyl borate sodium acetylide undergoes a palladium-catalyzed cross coupling with functionalized aryl halides or triflates in reasonable to good yields. The ethynylarenes thus obtained serve as building blocks for the formation of the highly effective tubulin polymerization inhibitors combretastatin A-4 (1) and A-5 (2) as well as for the synthesis of the plant-growth regulator lunularic acid (36).