Dedicated to Professor Horst Kessler on the occasion of his 75th birthday.
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 History and Importance of (Fungal) Secondary Metabolites
2 Reasons for the Synthesis of Fungal Natural Products
3 Total Syntheses of Selected Fungal Natural Products
3.1 Terpenes
3.1.1 Sesquiterpenes
3.1.1.1 Polyquinanes
3.1.1.2 Drimanes
3.1.2 Diterpenes: Cyathanes
3.1.3 Terpenes Containing a Butenolide Moiety
3.2 Alkaloids
3.3 Natural Products Derived from the Shikimate Pathway
3.3.1 Pulvinic Acid Derivatives and Terphenyl Quinones
3.3.2 Shikimate Pathway Derived Macrolides
3.3.3 Strobilurins
3.4 Aromatic Polyketides
3.4.1 Quinones
3.4.2 Resorcylates and Catechols
3.5 Sugar Derivatives
4 Conclusion and Outlook
Key words
biological activity - biomimetic synthesis - fungi - natural products - total synthesis