Total Synthesis and Antimicrobial Activities of All Stereoisomers of (16Z,20E)-Eushearilide and (16E,20E)-Eushearilide

• DOI: 10.1021/acs.joc.8b00774
• Publication Date: 2018-05-31T09:33:50Z
• Authors: Takayuki Tonoi; Takehiko Inohana; Teruyuki Sato; Tomoki Yoshida; Isamu Shiina
• Keywords: Anti-Infective Agents; Cyclization; Phosphorylcholine; Stereoisomerism; Chemistry Techniques, Synthetic; Macrolides; 01 natural sciences; 0104 chemical sciences

As promising antifungal agents, the eight stereoisomers of eushearilide, including natural compound, were synthesized relying on an asymmetric Mukaiyama aldol reaction, Julia-Kocienski olefination, and Shiina macrolactonization. Moreover, their in vitro antimicrobial activities against some fungi bacteria evaluated by disk-diffusion method, which revealed that not only eushearilide but also its exhibited significant activity a variety bacteria.