title: Enantioselective total synthesis of naturally occurring eushearilide and evaluation of its antifungal activity.
abstract: The asymmetric total synthesis of a newly proposed structure of (3S,16E,20E,23S)-(+)-eushearilide was achieved primarily through an asymmetric Mukaiyama aldol reaction, Schlosser-modified Wittig reaction and 2-methyl-6-nitrobenzoic anhydride-mediated macrolactonization. Based on detailed spectroscopic analyses, the obtained synthetic compound was found to be identical to natural eushearilide. Therefore, we were able to determine the true structure of eushearilide. Moreover, the synthetic compound was found to exhibit significant in vitro antifungal activity against various fungi and bacteria.
authors.affiliation: Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, Tokyo, Japan.
authors.forename: Takayuki
authors.initials: T
authors.lastname: Tonoi
authors.affiliation: Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, Tokyo, Japan.
authors.forename: Ryo
authors.initials: R
authors.lastname: Kawahara
authors.affiliation: Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, Tokyo, Japan.
authors.forename: Takehiko
authors.initials: T
authors.lastname: Inohana
authors.affiliation: Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, Tokyo, Japan.
authors.forename: Isamu
authors.initials: I
authors.lastname: Shiina
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D005658:Fungi / Q000187:drug effects*; D018942:Macrolides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D010767:Phosphorylcholine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013057:Spectrum Analysis; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D018942:Macrolides; C515840:eushearilide; D010767:Phosphorylcholine
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