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

Bidragsytere:
  • Britt Paulsen og
  • Lise-Lotte Gundersen

Tidsskrift

European Journal of Organic Chemistry
ISSN 1434-193X
e-ISSN 1099-0690
NVI-nivå 1

Om resultatet

Vitenskapelig artikkel
Publiseringsår: 2020
Publisert online: 2020
Trykket: 2020
Hefte: 15
Sider: 2244 - 2250

Importkilder

Scopus-ID: 2-s2.0-85083057821

Beskrivelse Beskrivelse

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.

Bidragsytere

Britt Paulsen

  • Tilknyttet:
    Forfatter
    ved Kjemisk institutt ved Universitetet i Oslo

Lise-Lotte Gundersen

  • Tilknyttet:
    Forfatter
    ved Organisk kjemi ved Universitetet i Oslo
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