Total synthesis of decahydroquinoline poison frog alkaloids ent-cis-195a and cis-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*

*この論文の責任著者

研究成果: ジャーナルへの寄稿学術論文査読

5 被引用数 (Scopus)

抄録

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.

本文言語英語
論文番号7529
ジャーナルMolecules
26
24
DOI
出版ステータス出版済み - 2021/12/01

ASJC Scopus 主題領域

  • 分析化学
  • 化学(その他)
  • 分子医療
  • 薬科学
  • 創薬
  • 物理化学および理論化学
  • 有機化学

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