Synthesis of Secondary Metabolites from Higher Fungi

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

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