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Total Synthesis of Decahydroquinoline Poison Frog Alkaloids ent-cis-195A and cis-211A.
Okada, Takuya; Wu, Naizhen; Takashima, Katsuki; Ishimura, Jungoh; Morita, Hiroyuki; Ito, Takuya; Kodama, Takeshi; Yamasaki, Yuhei; Akanuma, Shin-Ichi; Kubo, Yoshiyuki; Hosoya, Ken-Ichi; Tsuneki, Hiroshi; Wada, Tsutomu; Sasaoka, Toshiyasu; Shimizu, Takahiro; Sakai, Hideki; Dwoskin, Linda P; Hussaini, Syed R; Saporito, Ralph A; Toyooka, Naoki.
Afiliação
  • Okada T; Graduate School of Innovative Life Science, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan.
  • Wu N; Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan.
  • Takashima K; Graduate School of Science and Engineering, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan.
  • Ishimura J; Graduate School of Science and Engineering, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan.
  • Morita H; Institute of Natural Medicine, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan.
  • Ito T; Institute of Natural Medicine, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan.
  • Kodama T; Faculty of Pharmacy, Osaka Ohtani University, Tondabayashi, Osaka 584-8540, Japan.
  • Yamasaki Y; Institute of Natural Medicine, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan.
  • Akanuma SI; Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan.
  • Kubo Y; Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan.
  • Hosoya KI; Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan.
  • Tsuneki H; Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan.
  • Wada T; Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan.
  • Sasaoka T; Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan.
  • Shimizu T; Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan.
  • Sakai H; Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan.
  • Dwoskin LP; Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan.
  • Hussaini SR; Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, KY 40536, USA.
  • Saporito RA; Department of Chemistry and Biochemistry, The University of Tulsa, 800 S. Tucker Dr., Tulsa, OK 74104, USA.
  • Toyooka N; Department of Biology, John Carroll University, University Heights, OH 44118, USA.
Molecules ; 26(24)2021 Dec 12.
Article em En | MEDLINE | ID: mdl-34946611
ABSTRACT
The total synthesis of two decahydroquinoline poison frog alkaloids ent-cis-195A and cis-211A were achieved in 16 steps (38% overall yield) and 19 steps (31% overall yield), respectively, starting from known compound 1. Both alkaloids were synthesized from the common key intermediate 11 in a divergent fashion, and the absolute stereochemistry of natural cis-211A was determined to be 2R, 4aR, 5R, 6S, and 8aS. Interestingly, the absolute configuration of the parent decahydroquinoline nuclei of cis-211A was the mirror image of that of cis-195A, although both alkaloids were isolated from the same poison frog species, Oophaga (Dendrobates) pumilio, from Panama.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Quinolinas / Alcaloides Limite: Animals País/Região como assunto: America central / Panama Idioma: En Revista: Molecules Ano de publicação: 2021 Tipo de documento: Article
Texto completo
Imprimir
XML
PubMed Links
Buscar no Google

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Quinolinas / Alcaloides Limite: Animals País/Região como assunto: America central / Panama Idioma: En Revista: Molecules Ano de publicação: 2021 Tipo de documento: Article