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Total Synthesis and Antimicrobial Activities of All Stereoisomers of (16 Z,20 E)-Eushearilide and (16 E,20 E)-Eushearilide.
Tonoi, Takayuki; Inohana, Takehiko; Sato, Teruyuki; Yoshida, Tomoki; Shiina, Isamu.
Affiliation
  • Tonoi T; Department of Applied Chemistry, Faculty of Science , Tokyo University of Science , 1-3 Kagurazaka , Shinjuku-ku, Tokyo 162-8601 , Japan.
  • Inohana T; Department of Applied Chemistry, Faculty of Science , Tokyo University of Science , 1-3 Kagurazaka , Shinjuku-ku, Tokyo 162-8601 , Japan.
  • Sato T; Department of Applied Chemistry, Faculty of Science , Tokyo University of Science , 1-3 Kagurazaka , Shinjuku-ku, Tokyo 162-8601 , Japan.
  • Yoshida T; Department of Applied Chemistry, Faculty of Science , Tokyo University of Science , 1-3 Kagurazaka , Shinjuku-ku, Tokyo 162-8601 , Japan.
  • Shiina I; Department of Applied Chemistry, Faculty of Science , Tokyo University of Science , 1-3 Kagurazaka , Shinjuku-ku, Tokyo 162-8601 , Japan.
J Org Chem ; 83(15): 7886-7899, 2018 08 03.
Article in En | MEDLINE | ID: mdl-29847953
ABSTRACT
As promising antifungal agents, the eight stereoisomers of eushearilide, including the 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 and bacteria were evaluated by the disk-diffusion method, which revealed that not only natural eushearilide but also its stereoisomers exhibited significant antimicrobial activity against a variety of fungi and bacteria.
Subject(s)

Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Phosphorylcholine / Macrolides / Anti-Infective Agents Language: En Journal: J Org Chem Year: 2018 Type: Article Affiliation country: Japan

Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Phosphorylcholine / Macrolides / Anti-Infective Agents Language: En Journal: J Org Chem Year: 2018 Type: Article Affiliation country: Japan