The First Synthesis of (–)‐Agelasine F; an Antimycobacterial Natural Product Found in Marine Sponges in the Agelas Genus

(–)‐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. The first total synthesis of the bioactive marine natural product (–)‐agelasine F has been performed. The synthetic sequence starts with readily available (S)‐(+)‐ carvone which controls the stereochemistry in the target compound.