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Stereoselective Syntheses of trans-Anhydromevalonic Acid and trans-Anhydromevalonyl Group-Containing Natural Products.
Nakayama, Atsushi; Yasuno, Yoko; Yamamoto, Yuki; Saito, Kai; Kitsuwa, Kohei; Okamura, Hironori; Shinada, Tetsuro.
Affiliation
  • Nakayama A; Graduate School of Science, Osaka City University, 3-3-138, Sugimoto, Sumiyoshi, Osaka, 558-8585, Japan.
  • Yasuno Y; Graduate School of Science, Osaka City University, 3-3-138, Sugimoto, Sumiyoshi, Osaka, 558-8585, Japan.
  • Yamamoto Y; Graduate School of Science, Osaka City University, 3-3-138, Sugimoto, Sumiyoshi, Osaka, 558-8585, Japan.
  • Saito K; Graduate School of Science, Osaka City University, 3-3-138, Sugimoto, Sumiyoshi, Osaka, 558-8585, Japan.
  • Kitsuwa K; Graduate School of Science, Osaka City University, 3-3-138, Sugimoto, Sumiyoshi, Osaka, 558-8585, Japan.
  • Okamura H; Graduate School of Science, Osaka City University, 3-3-138, Sugimoto, Sumiyoshi, Osaka, 558-8585, Japan.
  • Shinada T; Graduate School of Science, Osaka City University, 3-3-138, Sugimoto, Sumiyoshi, Osaka, 558-8585, Japan.
J Nat Prod ; 85(4): 1052-1058, 2022 04 22.
Article in En | MEDLINE | ID: mdl-35195424
ABSTRACT
Collective total syntheses of trans-anhydromevalonic acid (tAHMA) and trans-anhydromevalonyl (tAHM) group-containing natural products (pestalotiopin A, pestalotiopamide C, pestalotiopamide D, farinomalein E, eleutherazine B, and trichocyclodipeptide A) were achieved using tAHMA esters as key intermediates. To this end, tAHMA tert-butyl ester was newly prepared by Z-vinyltosylation of tert-butyl 3-oxo-5-((triisopropylsilyl)oxy)pentanoate followed by the Negishi cross-coupling reaction with Me2Zn. tAHMA esters were converted to the target natural products via esterification or amidation. Comparison of the spectroscopic data of synthetic and natural products confirmed the E-configuration of the tAHM moieties in the natural products.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Biological Products Language: En Journal: J Nat Prod Year: 2022 Document type: Article Affiliation country: Japan
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Biological Products Language: En Journal: J Nat Prod Year: 2022 Document type: Article Affiliation country: Japan