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Proposal for structure revision of pinofuranoxin A through total syntheses of stereoisomers.
Ujiie, Kazuki; Tanaka, Chiaki; Arai, Masayoshi; Hashimoto, Masaru; Yoshida, Yuki; Kawano, Tomikazu; Tamura, Satoru.
Afiliación
  • Ujiie K; Laboratory of Natural Products Chemistry, School of Pharmaceutical Sciences, Wakayama Medical University, 25-1 Shichibancho, Wakayama, 640-8156, Japan.
  • Tanaka C; Laboratory of Natural Products Chemistry, School of Pharmaceutical Sciences, Wakayama Medical University, 25-1 Shichibancho, Wakayama, 640-8156, Japan.
  • Arai M; Laboratory of Natural Products for Drug Discovery, Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-Oka, Suita, Osaka, 565-0871, Japan.
  • Hashimoto M; Department of Biochemistry and Molecular Biology, Faculty of Agriculture and Life Science, Hirosaki University, 3-Bunkyo-Cho, Hirosaki, 036-8561, Japan.
  • Yoshida Y; Department of Medicinal and Organic Chemistry, School of Pharmacy, Iwate Medical University, 1-1-1 Idai-Dori, Yahaba-Cho, Shiwa-Gun, Iwate, 028-3694, Japan.
  • Kawano T; Department of Medicinal and Organic Chemistry, School of Pharmacy, Iwate Medical University, 1-1-1 Idai-Dori, Yahaba-Cho, Shiwa-Gun, Iwate, 028-3694, Japan.
  • Tamura S; Laboratory of Natural Products Chemistry, School of Pharmaceutical Sciences, Wakayama Medical University, 25-1 Shichibancho, Wakayama, 640-8156, Japan. s_tamura@wakayama-med.ac.jp.
J Nat Med ; 78(3): 608-617, 2024 Jun.
Article en En | MEDLINE | ID: mdl-38587582
ABSTRACT
The relative configuration of the epoxide functionality in pinofuranoxin A (1), α-alkylidene-ß-hydroxy-γ-methyl-γ-butyrolactone with trans-epoxy side chain isolated by Evidente et al. in 2021, was revised by DFT-based spectral reinvestigations and stereo-controlled synthesis. The present investigation demonstrates the difficulty of the configurational elucidation of the stereogenic centers on the conformationally flexible acyclic side-chains. Sharpless's enantioselective epoxidations and dihydroxylations were quite effective in the reinvestigations of the configurations. As our syntheses made all diastereomers available, these would be quite effective in the next structure-biological activity relationship studies.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: 4-Butirolactona Idioma: En Revista: J Nat Med Asunto de la revista: TERAPIAS COMPLEMENTARES Año: 2024 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Japón
Texto completo
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Imprimir
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: 4-Butirolactona Idioma: En Revista: J Nat Med Asunto de la revista: TERAPIAS COMPLEMENTARES Año: 2024 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Japón