Design, Synthesis, and Antifungal Activity of 16,17-Dihydroheronamide C and ent-Heronamide C.
Naoki KanohRyusei TerashimaHiromichi NishiyamaYuta TerajimaShota NagasawaYusuke SasanoYoshiharu IwabuchiHiroaki SaitoSyusuke EgoshiKosuke DodoMikiko SodeokaChengqian PanYoshinobu IkeuchiShinichi NishimuraHideaki KakeyaPublished in: The Journal of organic chemistry (2021)
16,17-Dihydroheronamide C (8) and ent-heronamide C (ent-1) were designed as probes for the mode-of-action analysis of heronamide C (1). These molecules were synthesized by utilizing a highly modular strategy developed in the preceding paper. The evaluation of the antifungal activity of these compounds revealed the exceptional importance of the C16-C17 double bond for the antifungal activity of heronamide C and the existence of chiral recognition between heronamide C (1) and cell membrane components.