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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.
Document Type
Article
Publication Date
12-12-2021
Digital Object Identifier (DOI)
https://doi.org/10.3390/molecules26247529
Related Content
The NMR spectra (1H-NMR, 13C-NMR) of all new compounds are available online.
Samples of cis-195A and cis-211A are available from the authors.
Repository Citation
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, "Total Synthesis of Decahydroquinoline Poison Frog Alkaloids ent-cis-195A and cis-211A" (2021). Pharmaceutical Sciences Faculty Publications. 200.
https://uknowledge.uky.edu/ps_facpub/200
Supplementary file
Notes/Citation Information
Published in Molecules, v. 26, issue 24, 7529.
© 2021 by the authors. Licensee MDPI, Basel, Switzerland.
This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).