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Terrazoanthines, 2-aminoimidazole alkaloids from the tropical eastern pacific zoantharian terrazoanthus onoi

Guillen, Paul O.
Jaramillo, Karla B.
Genta-Jouve, Gregory
Sinniger, Frederic
Rodriguez, Jenny
Thomas, Olivier P.
Repository DOI
Publication Date
2017-03-23
Type
Article
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Citation
Guillen, Paul O. Jaramillo, Karla B.; Genta-Jouve, Gregory; Sinniger, Frederic; Rodriguez, Jenny; Thomas, Olivier P. (2017). Terrazoanthines, 2-aminoimidazole alkaloids from the tropical eastern pacific zoantharian terrazoanthus onoi. Organic Letters 19 (7), 1558-1561
Abstract
The first chemical study of the common species Terrazoanthus onoi, present off the coast of Ecuador, led to the identification of a new family of 2-aminoimidazole alkaloids named terrazoanthines A-C (1-3). Homologues 1 and 2 feature an unprecedented 6-(imidazol-5-yl)benzo[d]-imidazole. Acyl substitution pattern and complete configurational assignments were deduced from comparison between experimental and theoretical C-13 NMR and ECD data, respectively. These compounds may represent key derivatives in the biosynthesis of zoanthoxanthins.
Funder
Publisher
American Chemical Society (ACS)
Publisher DOI
10.1021/acs.orglett.7b00369
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Attribution-NonCommercial-NoDerivs 3.0 Ireland