title: Total synthesis and stereochemical determination of yoshinone A.
abstract: In 2014, the γ-pyrone-containing polyketide, yoshinone A, was isolated from the marine cyanobacterium Leptolyngbya sp. and its structure was determined. Yoshinone A inhibited differentiation of 3T3-L1 cells into adipocytes, with an EC50value of 420 nM without any cytotoxicity, and therefore is expected to be a lead compound for obesity drugs. To establish its absolute configuration, and to provide sufficient amounts for further research, the total synthesis of yoshinone A was achieved through synthesis of its two possible diastereomers.
authors.affiliation: Department of Chemistry, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan.
authors.forename: Seiichi
authors.initials: S
authors.lastname: Shinomiya
authors.affiliation: Department of Chemistry, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan.
authors.forename: Arihiro
authors.initials: A
authors.lastname: Iwasaki
authors.affiliation: Department of Chemistry and Life Science, Kogakuin University, 2665-1, Nakano-Machi, Hachioji, Tokyo 192-0015, Japan.
authors.forename: Osamu
authors.initials: O
authors.lastname: Ohno
authors.affiliation: Department of Chemistry, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan. Electronic address: suenaga@chem.keio.ac.jp.
authors.forename: Kiyotake
authors.initials: K
authors.lastname: Suenaga
mesh_terms: D016475:3T3 Cells; D017667:Adipocytes / Q000187:drug effects; D000818:Animals; D002454:Cell Differentiation; D000458:Cyanobacteria / Q000737:chemistry*; D008386:Marine Biology; D051379:Mice; D061065:Polyketides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D011753:Pyrones / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D061065:Polyketides; D011753:Pyrones; C000614361:yoshinone A
keywords: Leptolyngbya sp.; Marine cyanobacteria; Polyketide; Total synthesis; Yoshinone A