Total Synthesis, Absolute Configuration, and Biological Activity of Xyloallenoide A

Abstract

AbstractThe novel natural product xyloallenoide A, isolated from the marine mangrove endophytic fungus from the South China Sea, and its diastereoisomer xyloallenoide A1, which contain N‐methyl‐substituted amino acids, were synthesized. The absolute configurations of the amino acid units of xyloallenoide A were finally confirmed to be L‐Lys, Me‐D‐Val, and Me‐L‐Ala. This report represents a practical and attractive alternative for the synthesis of N‐methyl‐substituted cyclotripeptides. In the preliminary bioassay, synthetic xyloallenoide A showed marginal activities against KB (IC50=9.6 μM) and KBv200 cells (IC50=10.3 μM), and xyloallenoide A1 was inactive against KB and KBv200 cells.