1. Total Synthesis of Decahydroquinoline Poison Frog Alkaloids ent- cis -195A and cis -211A.
- Author
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Okada T, Wu N, Takashima K, Ishimura J, Morita H, Ito T, Kodama T, Yamasaki Y, Akanuma SI, Kubo Y, Hosoya KI, Tsuneki H, Wada T, Sasaoka T, Shimizu T, Sakai H, Dwoskin LP, Hussaini SR, Saporito RA, and Toyooka N
- Subjects
- Alkaloids chemistry, Animals, Anura, Molecular Structure, Panama, Quinolines chemistry, Stereoisomerism, Alkaloids chemical synthesis, Quinolines chemical synthesis
- 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 2 R , 4a R , 5 R , 6 S , and 8a S . 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.
- Published
- 2021
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