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Total Synthesis of Decahydroquinoline Poison Frog Alkaloids ent- cis -195A and cis -211A.
- Source :
-
Molecules (Basel, Switzerland) [Molecules] 2021 Dec 12; Vol. 26 (24). Date of Electronic Publication: 2021 Dec 12. - Publication Year :
- 2021
-
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.
Details
- Language :
- English
- ISSN :
- 1420-3049
- Volume :
- 26
- Issue :
- 24
- Database :
- MEDLINE
- Journal :
- Molecules (Basel, Switzerland)
- Publication Type :
- Academic Journal
- Accession number :
- 34946611
- Full Text :
- https://doi.org/10.3390/molecules26247529