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

Abstract

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 [a]

Ozonolytic transformations of (R)‐(−)‐carvon in the presence of pyridine

“…Carvone 1 is a menthane monoterpenoid, a component of essential oils of cumin and dill, Mentha spicata known for its antimicrobial, nematicidal, antitumor, and plant growth regulating properties. [ 1 ] S ‐ and R ‐carvones are actively used in the synthesis of compounds with practically important properties: sesqui‐ [ 2–6 ] and diterpenes, [ 7–9 ] alkaloids, [ 10,11 ] macrolides, [ 12 ] insect pheromones, [ 13–15 ] and steroid systems. [ 16,17 ]…”

“…Carvone 1 is a menthane monoterpenoid, a component of essential oils of cumin and dill, Mentha spicata known for its antimicrobial, nematicidal, antitumor, and plant growth regulating properties. [1] S-and R-carvones are actively used in the synthesis of compounds with practically important properties: sesqui- [2][3][4][5][6] and diterpenes, [7][8][9] alkaloids, [10,11] macrolides, [12] insect pheromones, [13][14][15] and steroid systems. [16,17] This terpenoid is interesting as a substrate for chemical transformations due to the simultaneous presence of disubstituted and conjugated double bonds in the structure.…”