Molecules (Dec 2021)
Total Synthesis of Decahydroquinoline Poison Frog Alkaloids ent-<i>cis</i>-195A and <i>cis</i>-211A
- Takuya Okada,
- Naizhen Wu,
- Katsuki Takashima,
- Jungoh Ishimura,
- Hiroyuki Morita,
- Takuya Ito,
- Takeshi Kodama,
- Yuhei Yamasaki,
- Shin-ichi Akanuma,
- Yoshiyuki Kubo,
- Ken-ichi Hosoya,
- Hiroshi Tsuneki,
- Tsutomu Wada,
- Toshiyasu Sasaoka,
- Takahiro Shimizu,
- Hideki Sakai,
- Linda P. Dwoskin,
- Syed R. Hussaini,
- Ralph A. Saporito,
- Naoki Toyooka
Affiliations
- Takuya Okada
- Graduate School of Innovative Life Science, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan
- Naizhen Wu
- Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan
- Katsuki Takashima
- Graduate School of Science and Engineering, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan
- Jungoh Ishimura
- Graduate School of Science and Engineering, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan
- Hiroyuki Morita
- Institute of Natural Medicine, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan
- Takuya Ito
- Institute of Natural Medicine, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan
- Takeshi Kodama
- Institute of Natural Medicine, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan
- Yuhei Yamasaki
- Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan
- Shin-ichi Akanuma
- Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan
- Yoshiyuki Kubo
- Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan
- Ken-ichi Hosoya
- Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan
- Hiroshi Tsuneki
- Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan
- Tsutomu Wada
- Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan
- Toshiyasu Sasaoka
- Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan
- Takahiro Shimizu
- Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan
- Hideki Sakai
- Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan
- Linda P. Dwoskin
- Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, KY 40536, USA
- Syed R. Hussaini
- Department of Chemistry and Biochemistry, The University of Tulsa, 800 S. Tucker Dr., Tulsa, OK 74104, USA
- Ralph A. Saporito
- Department of Biology, John Carroll University, University Heights, OH 44118, USA
- Naoki Toyooka
- Graduate School of Innovative Life Science, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan
- DOI
- https://doi.org/10.3390/molecules26247529
- Journal volume & issue
-
Vol. 26,
no. 24
p. 7529
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.
Keywords
