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Total Synthesis of Decahydroquinoline Poison Frog Alkaloids ent-cis-195A and cis-211A.

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.

SUBMITTER: Okada T

PROVIDER: S-EPMC8706607 | biostudies-literature | 2021 Dec

REPOSITORIES: biostudies-literature

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Total Synthesis of Decahydroquinoline Poison Frog Alkaloids ent-cis-195A and cis-211A.

Okada Takuya T Wu Naizhen N Takashima Katsuki K Ishimura Jungoh J Morita Hiroyuki H Ito Takuya T Kodama Takeshi T Yamasaki Yuhei Y Akanuma Shin-Ichi SI Kubo Yoshiyuki Y Hosoya Ken-Ichi KI Tsuneki Hiroshi H Wada Tsutomu T Sasaoka Toshiyasu T Shimizu Takahiro T Sakai Hideki H Dwoskin Linda P LP Hussaini Syed R SR Saporito Ralph A RA Toyooka Naoki N

Molecules (Basel, Switzerland) 20211212 24

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</i ...[more]

PMID: 34946611

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