Tetrahedron letters

Practical synthesis of biaryl colchicinoids containing 3′, 4′-catechol ether-based A-rings via Suzuki cross-coupling with ligandless palladium in water

AM Deveau, TL Macdonald

Index: Deveau, Amy Morin; Macdonald, Timothy L. Tetrahedron Letters, 2004 , vol. 45, # 4 p. 803 - 807

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Citation Number: 29

Abstract

Eight new biaryl colchicinoids containing 3′, 4′-methylene or benzodioxy ether bridges were synthesized. The key synthetic step employed a ligandless, aqueous Suzuki cross- coupling reaction catalyzed by Pd (OAc) 2 with tetrabutylammonium bromide (TBAB) and potassium carbonate (K2CO3). The biaryl Suzuki products were typically formed in 5–30min and always in less than 1h.