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Total Synthesis of Sophoraflavanone H and Confirmation of Its Absolute Configuration.
Murakami, Haruka; Asakawa, Tomohiro; Muramatsu, Yoshihiro; Ishikawa, Ryo; Hiza, Aiki; Tsukaguchi, Yuta; Tokumaru, Yohei; Egi, Masahiro; Inai, Makoto; Ouchi, Hitoshi; Yoshimura, Fumihiko; Taniguchi, Tohru; Ishikawa, Yoshinobu; Kondo, Mitsuru; Kan, Toshiyuki.
Afiliação
  • Murakami H; School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga, Shizuoka, Shizuoka 422-8526, Japan.
  • Asakawa T; School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga, Shizuoka, Shizuoka 422-8526, Japan.
  • Muramatsu Y; Department of Fisheries-Food Science, Tokai University, 3-20-1 Orido, Shimizu, Shizuoka, Shizuoka 424-8610, Japan.
  • Ishikawa R; School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga, Shizuoka, Shizuoka 422-8526, Japan.
  • Hiza A; School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga, Shizuoka, Shizuoka 422-8526, Japan.
  • Tsukaguchi Y; School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga, Shizuoka, Shizuoka 422-8526, Japan.
  • Tokumaru Y; School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga, Shizuoka, Shizuoka 422-8526, Japan.
  • Egi M; School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga, Shizuoka, Shizuoka 422-8526, Japan.
  • Inai M; School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga, Shizuoka, Shizuoka 422-8526, Japan.
  • Ouchi H; School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga, Shizuoka, Shizuoka 422-8526, Japan.
  • Yoshimura F; School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga, Shizuoka, Shizuoka 422-8526, Japan.
  • Taniguchi T; School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga, Shizuoka, Shizuoka 422-8526, Japan.
  • Ishikawa Y; Faculty of Advanced Life Science, Frontier Research Center for Advanced Material and Life Science, Hokkaido University, Kita 21 Nishi 11, Sapporo, Hokkaido 001-0021, Japan.
  • Kondo M; School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga, Shizuoka, Shizuoka 422-8526, Japan.
  • Kan T; Graduate School of Science and Technology, Shizuoka University, 836 Ohya, Suruga, Shizuoka, Shizuoka 422-8529, Japan.
Org Lett ; 22(10): 3820-3824, 2020 05 15.
Article em En | MEDLINE | ID: mdl-32324417
ABSTRACT
Sophoraflavanone H (1) is a polyphenol with a hybrid-type structure containing 2,3-diaryl-2,3-dihydrobenzofuran and flavanone ring moieties. This compound and related analogues are promising leads for antimicrobial and antitumor drug development. Here we describe a total synthesis of 1 and its diastereomer. The dihydrobenzofuran and flavanone rings were constructed by a Rh-catalyzed asymmetric C-H insertion reaction and selective oxy-Michael reaction. The absolute configuration of 1 was established by X-ray crystallographic analysis and CD spectral investigation of synthetic derivatives.
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Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2020 Tipo de documento: Article
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Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2020 Tipo de documento: Article