Design and synthesis of novel pinacolylboronate containing combretastatin ‘antimitotic agent’ analogues

✍ Scribed by Bhaskar C. Das; Sakkarapalayam M. Mahalingam; Todd Evans

• Book ID: 104096513
• Publisher: Elsevier Science
• Year: 2009
• Tongue: French
• Weight: 798 KB
• Volume: 50
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2009.04.003

✦ Synopsis

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.