1404069-64-2Relevant academic research and scientific papers
Synthesis and biological evaluation of a potent salicylihalamide A lactam analogue
Balan, Dan,Burns, Christopher J.,Fisk, Nicholas G.,Hügel, Helmut,Huang, David C. S.,Segal, David,White, Charlotte,Wagler, J?rg,Rizzacasa, Mark A.
, p. 8147 - 8153 (2012/11/07)
The first synthesis of a lactam analogue 3 of salicylihalamide A (1) is reported. A key step in the approach was a photochemical acylation coupling between amine 10 and dioxinone 9 to form the amide 19. Acetylation followed by RCM with Grubbs 1st generation catalyst gave the desired E-lactam 23 (E:Z ratio 87:13) as the major compound. Conversion of macrolactam 23 into the vinyl iodide 26 followed by Cu catalysed cross coupling with the diene amide 7 gave aza-salicylihalamide analogue 3 in good yield. This compound demonstrated potent activity against several human leukaemia cell lines.
