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Design and synthesis of novel pinacolylboronate containing combretastatin 'antimitotic agent' analogues.

ABSTRACT: We developed a procedure to synthesize pinacolyl boronate containing stilbene derivatives and used this procedure to synthesize boron-containing combretastatin analogues. The key step involves the Wittig reaction of the ylide 4-(4,4,5,5-tetramethyl-1,3,2-dioxaboratophenyl)-methyl triphenylphosphonium bromide 11 with 3,4,5-trimethoxy benzaldehyde in the presence of (t)BuONa in DMF, providing 88% yield. We are now in a position to evaluate the biological activity of these derivatives as modulators of TGF-beta signaling pathways.

SUBMITTER: Das BC 

PROVIDER: S-EPMC2791373 | biostudies-literature | 2009 Jun

REPOSITORIES: biostudies-literature

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Design and synthesis of novel pinacolylboronate containing combretastatin 'antimitotic agent' analogues.

Das Bhaskar C BC   Mahalingam Sakkarapalayam M SM   Evans Todd T  

Tetrahedron letters 20090601 25

We developed a procedure to synthesize pinacolyl boronate containing stilbene derivatives and used this procedure to synthesize boron-containing combretastatin analogues. The key step involves the Wittig reaction of the ylide 4-(4,4,5,5-tetramethyl-1,3,2-dioxaboratophenyl)-methyl triphenylphosphonium bromide 11 with 3,4,5-trimethoxy benzaldehyde in the presence of (t)BuONa in DMF, providing 88% yield. We are now in a position to evaluate the biological activity of these derivatives as modulators  ...[more]

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