1185870-91-0Relevant articles and documents
Asymmetric syntheses and Wnt signal inhibitory activity of melleumin A and four analogues of melleumins A and B
Luo, Jie-Min,Dai, Chao-Feng,Lin, Shu-Yong,Huang, Pei-Qiang
, p. 328 - 335 (2009)
The first total synthesis of melleumin A and four analogues of melleumins A and B is described. The N-acyl L-Thr-Gly/β-hydroxy-γ-amino acid coupling/macrolactamization strategy allowed the efficient assembly of the three segments being free of epimerization. While the Jouin-Castro method with minor modification allows a rapid entrance to the key syn-β-hy-droxy-y-amino acid segment, required for the synthesis of melleumin A, an extension of our malimide-based methodology using a changed N-protecting group affords a flexible access to several anti-β-hydroxy-γ-amino acids, and hence analogues of melleumins A and B. Among them, unnatural 4-epi-melleumin B (2a) exhibits a modest inhibitory activity on Wnt signaling. The total synthesis of melleumin A allowed confirmation of its full structure.
