1. Total Synthesis of Decahydroquinoline Poison Frog Alkaloids ent- cis -195A and cis -211A.
- Author
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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., and Toyooka, Naoki
- Subjects
DENDROBATIDAE ,MIRROR images ,STEREOCHEMISTRY - 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. [ABSTRACT FROM AUTHOR]
- Published
- 2021
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