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The First Synthesis of (–)‐Agelasine F; an Antimycobacterial Natural Product Found in Marine Sponges in the Agelas Genus
Author(s) -
Paulsen Britt,
Gundersen LiseLotte
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000202
Subject(s) - antimycobacterial , chemistry , natural product , diterpene , stereochemistry , terpenoid , sponge , total synthesis , carvone , terpene , cancer cell lines , combinatorial chemistry , cancer cell , botany , biology , cancer , mycobacterium tuberculosis , medicine , tuberculosis , pathology , chromatography , essential oil , limonene , genetics
(–)‐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.