Marine Natural Products (Topics in Heterocyclic Chemistry, 58)

✍ Scribed by Hiromasa Kiyota (editor)

• Publisher: Springer
• Year: 2021
• Tongue: English
• Leaves: 510
• Category: Library

✦ Synopsis

This book is a compilation of the latest achievements of leading researchers in marine natural products with extremely diverse structures and biological activities. It presents discussions of isolation, structure elucidation, biosynthesis, total synthesis, and biochemical properties of the compounds with characteristic structures such as macrolides, cyclic depsipeptides, alkaloids, and water-soluble heterocyclic low-molecular-weight compounds, from sponges, bacteria, cyanobacteria, flagellates, and other such organisms. The book especially focuses on heterocyclic natural products as a title in the book series, Topics in Heterocyclic Chemistry.

✦ Table of Contents

Preface
Contents
Part I: Isolation, Synthesis and Bioorganic Studies on Marine Alkaloids
Manzamines: Marine Bioactive Heterocycles
1 Introduction
1.1 Discovery
1.2 Biological Activities
1.3 Biosynthesis
2 Recently Isolated Unique Manzamine Derivatives
2.1 Zamamidines A-D
2.2 Acanthomanzamines A-E
2.3 Kepulauamine A
2.4 Acantholactone and Acantholactam
2.5 Pre-neo-kauluamine
3 Recently Reported Biological Activities
3.1 Inhibition of the Proteasome
3.2 Anti-atherosclerotic Activity
4 Conclusions
References
Total Synthesis of Manzamine Alkaloids
1 Introduction
1.1 Isolation and Biological Properties of the Most Prominent Manzamine Alkaloids
2 Synthetic Approaches to Manzamine Alkaloids
3 Nakadomarin A
3.1 Total Synthesis of Nakadomarin A: First-Generation, Alkyne Metathesis [96]
3.2 Total Synthesis of Nakadomarin A: Second Generation, Alkyne Metathesis [97]
3.3 Total Synthesis of Nakadomarin A, Third Generation, Alkene Ring-Closing Metathesis [93]
4 Manzamine A [73]
5 Ircinal A and Ircinol A
6 Keramaphidin B [106]
7 Conclusion
References
Total Syntheses of the Dictyodendrins
1 Introduction
2 Biological Activity
3 Syntheses of the Dictyodendrins
3.1 Fürstner´s Total Syntheses of Dictyodendrins B, C, and E
3.2 Ishibashi´s Formal Synthesis of Dictyodendrin B
3.3 Tokuyama´s Total Syntheses of Dictyodendrins A-E
3.4 Jia´s Total Syntheses of Dictyodendrins B and E and Formal Synthesis of Dictyodendrin C
3.5 Yamaguchi/Itami/Davies´ Total Syntheses of Dictyodendrins A and F
3.6 Gaunt´s Total Synthesis of Dictyodendrin B
3.7 Ready´s Total Syntheses of Dictyodendrins F, H, and I
3.8 Ohno´s Total Syntheses of Dictyodendrins B, C, and F and Formal Syntheses of Dictyodendrins A and D
3.9 Guo/He´s Total Syntheses of Dictyodendrins F, G, H, and I
4 Conclusion
References
Marine Bioluminescence with Dehydrocoelenterazine, an Imidazopyrazinone Compound
1 Introduction
2 Watasenia scintillans
3 Symplectoteuthis (Sthenoteuthis) oualaniensis
4 Eucleoteuthis luminosa
5 Dosidicus gigas (The Largest Luminescent Animal in the World)
6 Pholas dactylus
7 Conclusion
References
Part II: Isolation and Synthesis of Water-Soluble Low Weight Molecular Compounds
Chemical and Biological Aspects of Water-Soluble Heterocyclic Marine Natural Products
1 Introduction
2 Discovery of Water-Soluble Marine Heterocycles
3 Excitatory Amino Acids
3.1 Kainic Acid
3.2 Dysiherbaines and Related Compounds
3.3 Sponge-Derived 4-Sulfooxypiperidine-2-Carboxylic Acids
4 Neuroactive Purine Derivatives from Marine Sponges
5 Tunicate-Derived Heterocyclic Molecules
5.1 Mellpaladines
5.2 Aromatics from Cnemidocarpa irene
6 Marine Polycations
7 Polyguanidine Alkaloids from Zoantharians
8 Mycosporines
9 Conclusion
References
Synthesis of Paralytic Shellfish Toxins: Saxitoxins
1 Introduction: Saxitoxin and Its Derivatives
2 Construction of Saxitoxin (STX) Core Structure via Nucleophilic Addition of Guanidine to Iminium Cation (First Generation St...
2.1 Synthesis of STX (1) by the Kishi Group
2.2 Synthesis of STX by the Du Bois Group
2.3 Synthesis of STX Derivative dc-α-STXol (10) by the Nishikawa Group
2.4 Synthesis of STX by the Nagasawa Group
3 Synthesis of STX Skeletons in Protected Forms and Its Application to the Synthesis of STX (1) and Its Natural Analogs
3.1 Synthesis of STX Skeleton in Protected Form and Synthesis of STX Analogs by the Du Bois Group
3.2 Synthesis of STX Skeleton in Protected Form and Synthesis of STX Analogs by the Nishikawa Group
3.3 Synthesis of STX Skeleton in Protected Form and Synthesis of STX Analogs by the Looper Group
3.4 Synthesis of STX Skeleton in Protected Form and Synthesis of STX Analogs by the Nagasawa Group
4 Summary and Outlook
References
Part III: Isolation and Synthesis of Low-Weight Molocular Compounds from Marine Bacteria Etc
Natural Products from Marine Bacteria and Actinomycetes
1 Introduction
2 Natural Products from Marine Bacteria
2.1 Dihydroisocoumarins
2.2 Arylthiazolines
2.3 Compounds from Labrenzia
2.4 Compounds from Microbulbifer
3 Natural Products from Marine Actinomycetes
3.1 Acylimidazoles
3.2 Rakicidins
3.3 Nocapyrones
4 Conclusion and Future Prospect
References
Siderophores from Fish Pathogenic Bacteria
1 Introduction
2 Vibriosis by Vibrio anguillarum
2.1 Anguibactin Iron-Uptake System
2.2 Vanchrobactin Iron-Uptake System
2.3 Piscibactin Iron-Uptake System
2.4 Distribution of Each Siderophore Iron-Uptake System and Their Role in the Virulence
3 Photobacteriosis by Photobacterium damselae subsp. piscicida
4 Furunculosis by Aeromonas salmonicida
5 Concluding Remarks
References
Marine Natural Products with Bioactivity Against Neglected Tropical Diseases
1 Introduction
1.1 Sources of Natural Products
1.2 Neglected Tropical Diseases
2 Marine Natural Products Active Against Leishmaniasis
2.1 Antileishmanial Sponge Metabolites
2.2 Antileishmanial Cnidaria Metabolites
2.3 Antileishmanial Algal Metabolites
2.4 Antileishmanial Echinoderm Metabolites
2.5 Antileishmanial Molluscan Metabolites
2.6 Antileishmanial Marine Fungal Metabolites
2.7 Antileishmanial Bacterial Metabolites
2.8 Antileishmanial Cyanobacterial Metabolites
3 Marine Natural Products Active Against Human African Trypanosomiasis
3.1 Sponge Metabolites Active Against the HAT Parasites
3.2 Cnidarian Metabolites Active Against HAT
3.3 Metabolites from Bryozoa Inhibiting Active Against HAT
3.4 Echinoderm Metabolites Active Against HAT
3.5 Ascidian Metabolites Active Against HAT
3.6 Marine Bacterial Metabolites Active Against HAT
3.7 Marine Cyanobacterial Metabolites with Activity Against HAT
4 Marine Natural Products Active Against Chagas Disease
4.1 Antitrypanosomal Sponge Metabolites Active Against Chagas Disease
4.2 Antitrypanosomal Algal Metabolites Active Against Chagas Disease
4.3 Antitrypanosomal Ascidian Metabolites Active Against Chagas Disease
4.4 Antitrypanosomal Marine Bacterial Metabolites Active Against Chagas Disease
4.5 Antitrypanosomal Marine Cyanobacterial Metabolites Active Against Chagas Disease
5 Marine Natural Products Active Against Schistosomiasis
6 Marine Natural Products Active Against Dengue
7 Marine Natural Products Active Against Chikungunya
8 Marine Natural Products Active Against Snakebite Envenoming
9 Marine Natural Products Active Against Trachoma
10 Marine Natural Products Active Against Soil-Transmitted Helminths (STH)
11 Buruli Ulcer
12 Dracunculiasis
13 Echinococcosis
14 Foodborne Trematodiasis
15 Leprosy
16 Lymphatic Filariasis
17 Mycetoma and Chromoblastomycosis
18 Onchocerciasis
19 Rabies
20 Scabies
21 Taeniasis/Cysticercosis
22 Yaws
23 Conclusion
References
Total Synthesis of the Amicoumacin Family of Natural Products
1 Introduction
2 AI-77-B
2.1 Hamada-Shioiri´s Total Synthesis of AI-77-B
2.2 Thomas´s Total Synthesis of AI-77-B
2.3 Procter´s Total Synthesis of AI-77-B
2.4 Vogel´s Total Synthesis of AI-77-B
2.5 Kotsuki´s Total Synthesis of AI-77-B
2.6 Ghosh´s Total Synthesis of AI-77-B
2.7 Rao´s Total Synthesis of AI-77-B
3 Bacilosarcins A-C
3.1 Enomoto-Kuwahara´s Total Synthesis of Bacilosarcins A-C
4 PM-94148 and Y-05460M-A
4.1 Py-Valleé´s Total Synthesis of PM-94128
4.2 Enomoto-Kuwahara´s Total Synthesis of PM-94128 and Y-05460M-A
5 Conclusion
References
Part IV: Isolation and Synthesis of Marine Macrolides, Cyclic Peptides, Depsipeptides Etc
Bioactive Substances from Marine Cyanobacteria
1 Introduction
2 Polyketides and Macrolides
2.1 Biselyngbyasides
2.1.1 Isolation and Structure
2.2 Koshikalide
2.3 Leptolyngbyolides
2.4 Kanamienamide
2.5 Hoshinolactam
2.6 Yoshinone A
2.7 Caldorin
3 Linear Peptides with Heterocycles
3.1 Bisebromoamides
3.2 Biseokeaniamides
4 Linear Peptides and Depsipeptides
4.1 Maedamide
4.2 Izenamides
4.3 Iheyamides
5 Lipopeptides
5.1 Kurahynes
5.2 Jahanyne Family
5.3 Hoshinoamides
5.4 Minnamide A
5.5 Mabuniamide
5.6 Ikoamide
6 Cyclic Peptides and Depsipeptides
6.1 Kurahamide
6.2 Janadolide
6.3 Urumamide
6.4 Kohamamides
6.5 Croissamide
7 Conclusion
References
Cyclic Depsipeptides, Callipeltins
1 Introduction
2 Isolation of Cyclic Depsipeptides
2.1 Distribution of Cyclic Depsipeptides in Marine Sponges
2.2 Isolation and Structural Analysis of Callipeltins
3 Preparation of Unusual Amino Acids
3.1 Preparation of β-MeOTyr and Determination of Absolute Structure
3.2 Preparation of 3-MeGln and Me2pyroGln
3.3 Preparation of AGDHE
3.4 Synthesis of TMHEA and Determination of Absolute Structure
3.5 Synthesis of D-alloThr
4 Total Synthesis of Cyclic Depsipeptides
4.1 Total Synthesis of Callipeltin B and Its Analogues
5 Summary and Perspective
References
Synthesis of Marine C2-Symmetrical Macrodiolide Natural Products
1 Introduction
2 Biogenetic Formation of Macrodiolide
3 Swinholide A
3.1 Paterson´s Total Synthesis of Swinholide A
3.2 Nicolaou´s Total Synthesis of Swinholide A
3.3 Krische´s Total Synthesis of Swinholide A
4 Clavosolide A
4.1 Lee´s Total Synthesis of Clavosolide A
4.2 Willis´s Total Synthesis of Clavosolide A
4.3 Smith´s Total Synthesis of Clavosolide A
4.4 Chakraborty´s Total Synthesis of Clavosolide A
4.5 Jennings´s Formal Synthesis of Clavosolide A
4.6 Floreancig´s Total Synthesis of Clavosolide A
4.7 Hong´s Total Synthesis of Clavosolide A
4.8 Breit´s Total Synthesis of Clavosolide A
4.9 Aggarwal´s Total Synthesis of Clavosolide A
4.10 Krische´s Total Synthesis of Clavosolide A
5 Cyanolide A
5.1 Hong´s Total Synthesis of Cyanolide A
5.2 Reddy´s Synthesis of Cyanolide A Aglycon
5.3 Rychnovsky´s Synthesis of Cyanolide A Aglycon
5.4 Bates´s Total Synthesis of Cyanolide A
5.5 Zhou´s Total Synthesis of Cyanolide A
6 Marinomycin A
6.1 Nicolaou´s Total Synthesis of Marinomycin A
6.2 Evans´s Total Synthesis of Marinomycin A
6.3 Cossy´s Synthesis of Marinomycin A Monomer
6.4 Hatakeyama´s Total Synthesis of Marinomycin A
7 Conclusion
References
Total Synthesis of (-)-Enigmazole A
1 Introduction
2 Total Synthesis of (-)-Enigmazole A by Molinski
3 Total Synthesis of (-)-Enigmazole A by Smith
4 Total Synthesis of (-)-Enigmazole A by Fürstner
5 Total Synthesis of (-)-Enigmazole A by Fuwa
6 Formal Synthesis of (-)-Enigmazole A by Kadota
7 Conclusions
References
Part V: Isolation and Synthesis of Middle-Weight Molecular Compounds with a Long Carbon Chain
Polyketides Biosynthesis in Marine Sponges of the Family Theonellidae
1 Introduction
2 Type I Polyketide Synthase and Non-ribosomal Peptide Synthetase
3 Onnamide-Type Compounds
4 Misakinolide-Type Compounds
5 Calyculin A
6 Discodermolide
7 Conclusion
References
Synthetic Studies of Serinolipids
1 Introduction
2 Synthetic Studies of Didemniserinolipid B
2.1 Isolation
2.2 Ley´s First Total Synthesis and Structure Revision
2.3 Burke´s Formal Total Synthesis
2.4 Ramana´s Formal Total Synthesis
2.5 Prasad´s Formal Total Synthesis
2.6 Chandrasekhar´s Formal Total Synthesis
2.7 Tong´s Formal Total Synthesis and Synthesis of Proposed Didemniserinolipid C
3 Synthetic Study of Cyclodidemniserinol Trisulfate
3.1 Isolation
3.2 Long´s Partial Synthesis
4 Synthetic Study of Siladenoserinols
4.1 Isolation
4.2 Doi´s First Total Synthesis of Siladenoserinol A
4.3 Tong´s Total Synthesis of Siladenoserinols A and H
5 Conclusion
References
Synthesis of Chlorosulfolipid Natural Products
1 Introduction
2 Isolation of Chlorosulfolipids
3 Structure Determination
4 Synthesis of Chlorosulfolipids
4.1 Carreira´s Synthesis of Mytilipin A
4.2 Vanderwal´s Synthesis of Mytilipin A
4.3 Yoshimitsu´s Synthesis of Mytilipin A
4.4 Burns Synthesis of Deschloromytilipin A
4.5 Vanderwal´s Synthesis of Danicalipin A
4.6 Umezuwa´s Synthesis of Danicalipin A
4.7 Yoshimitsu´s Synthesis of Danicalipin A
4.8 Carreira´s Synthesis of Danicalipin A
4.9 Burns´ Synthesis of Danicalipin A
4.10 Carreira´s Synthesis of Bromodanicalipin A and Fluorodanicalipin A
4.11 Vanderwal´s Synthesis of Malhamensilipin A
4.12 Denton´s Synthesis of (+)-Malhamensilipin A
4.13 Carreira´s Synthesis of Nominal Mytilipin B
4.14 Carreira´s Synthesis of Revised Mytilipin B
References
The Callipeltoside Story
1 Isolation
1.1 Structural Features and Assignment
1.1.1 Callipeltoside A
1.1.2 Callipeltosides B and C
1.2 Biological Activity of the Callipeltosides
1.2.1 Studies by Minale
1.2.2 Studies by Trost
2 Structural Investigations and Total Syntheses
2.1 Paterson Aglycon Synthesis (2001)
2.1.1 Retrosynthesis
2.1.2 Synthesis of the C1-C17 Vinyl Iodide
2.1.3 Synthesis of Enantiomeric trans-Chlorocyclopropyl Alkynes 12 and ent-12
2.1.4 Synthesis of Diastereomeric Aglycons 39 and 41
2.2 Trost Synthesis of Deschlorocallipeltoside A (8)
2.2.1 Retrosynthesis
2.2.2 Synthesis of the C1-C13 Macrocycle 44
2.2.3 Completion of the Deschlorocallipeltoside Aglycon 75
2.2.4 Synthesis of L-Callipeltose A (43) and Deschlorocallipeltoside A
2.3 Trost Synthesis of Callipeltoside A (2002)
2.3.1 Synthesis of Enantiomeric trans-Chlorocyclopropanes 84 and ent-84
2.3.2 Completion of Callipeltoside A (1)
2.3.3 Second-Generation Synthesis of the Callipeltoside Aglycon 86
2.4 Evans Synthesis of Callipeltoside A (2002)
2.4.1 Retrosynthesis
2.4.2 Synthesis of C1-C13 Fragment 91
2.4.3 Synthesis of trans-Chlorocyclopropane Sidechain 116
2.4.4 l-Callipeltose A Sugar 90
2.4.5 Completion of Callipeltoside A
2.5 Paterson Synthesis of Callipeltoside A (2003)
2.6 Panek Synthesis of Callipeltoside A (2004)
2.6.1 Retrosynthesis
2.6.2 Formation of C1-C10 Pyran 135
2.6.3 Synthesis of the C11-C22 Fragment
2.6.4 Synthesis of Callipeltose A
2.6.5 Completion of Callipeltoside A
2.7 Hoye Synthesis of Callipeltoside A (2010)
2.7.1 Retrosynthesis
2.7.2 Synthesis of the C1-C13 Fragment
2.7.3 Completion of Callipeltoside A
2.8 MacMillan Synthesis of Callipeltoside C (2008)
2.8.1 Retrosynthesis
2.8.2 Synthesis of Pyran 170
2.8.3 Formation of Vinyl Iodide 171
2.8.4 Fragment Union and Completion of the Aglycon (9)
2.8.5 Synthesis of d-Callipeltose C
2.8.6 Completion of Callipeltoside C
2.9 Ley Syntheses of Callipeltosides A, B and C (2012)
2.9.1 Retrosynthesis
2.9.2 Synthesis of Pyran 170
2.9.3 Completion of the C10-C22 Fragment
2.9.4 Union of Fragments 170 and 197 and Macrocycle Formation
2.9.5 Preparation of Callipeltose A, B and C Thioglycosides
2.9.6 Completion of Callipeltosides A, B and C
2.9.7 Stereochemistry of the Glycosidic Linkages of Callipeltosides B and C
Callipeltoside C
1JC-H Coupling Constant
NOESY Data
Callipeltoside B
3 Conclusion and Final Remarks
References