474254-69-8Relevant academic research and scientific papers
Total synthesis of (-)-salicylihalamide A and related congeners
Smith III, Amos B,Zheng, Junying
, p. 6455 - 6471 (2002)
A concise, highly efficient total synthesis of (-)-salicylihalamide A (1), a novel marine sponge metabolite, has been achieved. Key features of the synthetic strategy include a highly E-selective ring-closing metathesis to construct the 12-membered salicylihalamide A macrocycle and a practical method for installation of the labile ene-hepta-(Z,Z)-dienamide side chain involving N-acylation of enecabarmate 5, the latter derived from the corresponding α,β-unsaturated carboxylic acid 28 via acyl azide formation and thermal Curtius rearrangement. Two structurally simplified analogs (3 and 4) were also prepared which displayed significant, but attenuated cell growth inhibitory activity against several human tumor cell lines.
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.
