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Cristin-resultat-ID:
1811511
Sist endret:
2. oktober 2020, 14:02
NVI-rapporteringsår:
2020
Resultat
Vitenskapelig artikkel
2020
The first synthesis of (–)-agelasine F; an antimycobacterial natural product found in marine sponges in the Agelas genus
Britt Paulsen
og
Lise-Lotte Gundersen
Tidsskrift
Tidsskrift
European Journal of Organic Chemistry
ISSN 1434-193X
e-ISSN 1099-0690
NVI-nivå 1
Finn i kanalregisteret
Om resultatet
Om resultatet
Vitenskapelig artikkel
Publiseringsår: 2020
Publisert online: 2020
Trykket: 2020
Hefte: 15
Sider: 2244 - 2250
Lenker
Lenker
original online (doi)
https://doi.org/10.1002/ejoc.202000202
Importkilder
Importkilder
Scopus-ID: 2-s2.0-85083057821
Beskrivelse
Beskrivelse
Engelsk
Tittel
The first synthesis of (–)-agelasine F; an antimycobacterial natural product found in marine sponges in the Agelas genus
Sammendrag
(–)-Agelasine F (also known as ageline A) is a diterpene-adenine hybrid natural product isolated from marine sponges (Agelas species) and this compound is known to display cytotoxic activity against a variety of cancer cell lines as well as microorganisms. We herein report the first total synthesis of (–)-agelasine F. The commercially available and inexpensive monoterpenoid (S)-carvone was found to be a highly suitable starting material for the construction of the terpenoid part of the desired agelasine and controlling the stereochemistry of the target compound. Two alternative strategies from (S)-carvone were evaluated. Key-intermediates in the (–)-agelasine F synthesis are believed also to be valuable starting materials for total syntheses of other bioactive marine sponge metabolites. The synthetic route to (–)-agelasine F described herein is more efficient than previously published syntheses of racemic or ent-agelasine F.
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Bidragsytere
Bidragsytere
Britt Paulsen
Forfatter
ved Kjemisk institutt ved Universitetet i Oslo
Lise-Lotte Gundersen
Forfatter
ved Organisk kjemi ved Universitetet i Oslo
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