Synthesis of Secondary Metabolites from Higher Fungi

Abstract

Higher fungi are a promising source of new bioactive natural products with great structural diversity, ranging from polyketides to terpenoids and alkaloids. Many of these structures are a challenge for synthetic organic chemists who have been inspired to develop new total syntheses. Nevertheless, reviews covering syntheses of fungal natural products are lacking. One aim of this review is to close this gap and to present a selection of more recent syntheses of fungal secondary metabolites from different structural classes. Secondly, this review intends to demonstrate that there are many more motivations for the synthesis of natural products than to confirm a proposed structure or to report the first total synthesis of a new natural product. Thirdly, this review is intended to stimulate the interest of organic chemists in the synthesis of fungal natural products. 1

Mass Spectrometry: A Rosetta Stone to Learn How Fungi Interact and Talk

“…This pathway started with the condensation of phosphoenolpyruvate and erythrose 4-phosphate to give shikimic acid, and its final product is chorismate, which is the precursor of the synthesis for the amino acids: tryptophan, L-phenylalanine and L-tyrosine [10,54]. Chorismate is also the precursor of diverse fungal specialized metabolites such as pulvinones, terphenyl quinones, macrolides and strobilurins [8]. Although the shikimic acid pathway occurs in bacteria, plant and fungi, the distinct enzymatic processes in fungi make it different from that in plants and bacteria, and therefore structures of many shikimic acid-derived metabolites are particular to fungi [10].…”

“…Although the shikimic acid pathway occurs in bacteria, plant and fungi, the distinct enzymatic processes in fungi make it different from that in plants and bacteria, and therefore structures of many shikimic acid-derived metabolites are particular to fungi [10]. Shikimic acid-derived compounds can function as pigments and biocides [8].…”

“…Fungi have been very successful in inhabiting the world, and they can be found in terrestrial and aquatic environments, as symbiotic associations as well as saprophytic or parasitic organisms. Fungal ecological success is also a consequence of their huge metabolic machinery that allows them to produce diverse chemical compounds, which are important for their ecological interactions and survival [6][7][8][9].…”