Contents 3.3 Cephalosporins 3 4 Biosynthesis of B-Lactams 3.5 Metabolites Containing a Diketopiperazine Ring 39 % 3.5.2 Gliotoxi 3.6 The Cyclopenin-Viridicatin Group of Metabolites 3.7 Tryptophan-derived Metabolites 3.8 Glutamic Acid Derivatives 3.9 Fungal Peptides 45 Chapter 4 Polyketides from Fungi 4.1 Introduction 47 4.2 Polvketide Biosynthesis 48 4.3 Triketides 4.4 Tetraketides 51 4.4.1 6-Methylsalicylic Acid 4.4.2 Patulin and Penicillic Acid 443 Gladiolic Acid and its Relatives 4.4.4 Tetrake tide T nes 4.4.5 Mycophenolic Acid 567 4.5 Pentaketides 4.5.1 Citrinin 4.5.2 Terrein 4.6 Hepta-and Octaketides 4.6.1 Griseofulvin 61 4.6.2 Cladosporin(Asperentin) 47 Polyketide Lactones Statin Cytochalas ins 568 4.10 Fatty Acids from Fung 8 4.11 Polyacetylenes from the Higher Fungi 70 Chapter 5 Terpenoid Fungal Metabolites 5.1 Introduction D 3 osynthesis of Fungal Terpenoids Mo 54 Sesquiterpenoids 5.4.1 Cyclonerodiol 5.4.2 Helicobasidin 5.4.3 Trichothecenes 5.4.4 PR-Toxin 5.4.5Botryanes 81 3.3 Cephalosporins 36 3.4 Biosynthesis of b-Lactams 37 3.5 Metabolites Containing a Diketopiperazine Ring 39 3.5.1 Mycelianamide 40 3.5.2 Gliotoxin 40 3.6 The Cyclopenin-Viridicatin Group of Metabolites 42 3.7 Tryptophan-derived Metabolites 42 3.8 Glutamic Acid Derivatives 44 3.9 Fungal Peptides 45 Chapter 4 Polyketides from Fungi 4.1 Introduction 47 4.2 Polyketide Biosynthesis 48 4.3 Triketides 50 4.4 Tetraketides 51 4.4.1 6-Methylsalicylic Acid 51 4.4.2 Patulin and Penicillic Acid 52 4.4.3 Gladiolic Acid and its Relatives 55 4.4.4 Tetraketide Tropolones 56 4.4.5 Mycophenolic Acid 57 4.5 Pentaketides 58 4.5.1 Citrinin 58 4.5.2 Terrein 60 4.6 Hepta- and Octaketides 61 4.6.1 Griseofulvin 61 4.6.2 Cladosporin (Asperentin) 64 4.7 Polyketide Lactones 65 4.8 Statins 66 4.9 Cytochalasins 68 4.10 Fatty Acids from Fungi 68 4.11 Polyacetylenes from the Higher Fungi 70 Chapter 5 Terpenoid Fungal Metabolites 5.1 Introduction 73 5.2 Biosynthesis of Fungal Terpenoids 73 5.3 Monoterpenoids 76 5.4 Sesquiterpenoids 76 5.4.1 Cyclonerodiol 77 5.4.2 Helicobasidin 78 5.4.3 Trichothecenes 78 5.4.4 PR-Toxin 81 5.4.5 Botryanes 81 viii Contents