Cossy / Arseniyadis / Meyer Metathesis in Natural Product Synthesis

Strategies, Substrates and Catalysts
1. Auflage 2011
ISBN: 978-3-527-64208-3
Verlag: Wiley-VCH
Format: EPUB
Kopierschutz: Adobe DRM (»Systemvoraussetzungen)

E-Book, Englisch, 384 Seiten, E-Book

Diese übersichtlich strukturierte Monographie stellt die Bedeutung der Metathese für die Naturstoffsynthese in den Mittelpunkt der Diskussion. Ausführliche Erläuterungen zu den verschiedenen Typen von Schlüsselreaktionen fügen sich zu einem informativen Gesamtbild zusammen. Mit ausgewählten Synthesevorschriften!

Autoren/Hrsg.

Cossy, Janine

Arseniyadis, Stellios

Meyer, Christophe

Weitere Mitwirkende

Grubbs, Robert H.

Inhaltsverzeichnis

Preface

SYNTHESIS OF NATURAL PRODUCTS CONTAINING MEDIUM-SIZE CARBOCYCLES BY RING-CLOSING ALKENE METATHESIS

Introduction

Formation of Five-Membered Carbocycles by RCM

Formation of Six-Membered Carbocycles by RCM

Formation of Seven-Membered Carbocycles by RCM

Formation of Eight-Membered Carbocycles by RCM

Formation of Nine-Membered Carbocycles by RCM

Formation of 10-Membered Carbocycles by RCM

 

Conclusion

NATURAL PRODUCTS CONTAINING MEDIUM-SIZED NITROGEN HETEROCYCLES SYNTHESIZED BY RING-CLOSING ALKENE METATHESIS

Introduction

Five-Membered Nitrogen Heterocycles

Six-Membered Nitrogen Heterocycles

Seven-Membered Nitrogen Heterocycles

Eight-Membered Nitrogen Heterocycles

Conclusion

SYNTHESIS OF NATURAL PRODUCTS CONTAINING MEDIUM-SIZE OXYGEN HETEROCYCLES BY RING-CLOSING ALKENE METATHESIS

Introduction

General RCM Approaches to Medium Rings

Laurencin

Eunicellins/Eleutherobin

Helianane

Octalactin A

Microcarpalide and the Herbarums

Marine Ladder Toxins

Conclusion

PHOSPHOROUS AND SULFUR HETEROCYCLES VIA RING-CLOSING METATHESIS: APPLICATION IN NATURAL PRODUCT SYNTHESIS

Introduction

Synthesis and Reactivity of Sulfones Derived from RCM

Total Synthesis of the Originally Proposed Structure of (±)-Mycothiazole

Synthesis and Reactivity of Phosphates from RCM

Applications of Phosphate Tethers in the Synthesis of Dolabelide C

Conclusion

SYNTHESIS OF NATURAL PRODUCTS CONTAINING MACROCYCLES BY ALKENE RING-CLOSING METATHESIS

Introduction

Organization of the Chapter

Macrocyclic Polyketides

Terpenoids

Macrocyclic Lipids

Macrocyclic Glycolipids

Conclusions and Outlook

SYNTHESIS OF NATURAL PRODUCTS AND RELATED COMPOUNDS USING ENE-YNE METATHESIS

Introduction

Synthesis of Natural Products and Related Compounds Using Ene-Yne Metathesis

Synthesis of Natural Products and Related Compounds Using Ene-Yne Cross-Metathesis (CM)

Synthesis of Natural Products Using Skeletal Reorganization

RING-CLOSING ALKYNE METATHESIS IN NATURAL PRODUCT SYNTHESIS

Introduction

Alkyne Metathesis

Ring-Closing Alkyne Metathesis

Applications of RCAM in Natural Product Synthesis

Conclusions

TEMPORARY SILICON-TETHERED RING-CLOSING METATHESIS REACTIONS IN NATURAL PRODUCT SYNTHESIS

Introduction

Temporary Silicon-Tethered Ring-Closing Metathesis Reactions

Conclusions and Outlook

METATHESIS INVOLVING A RELAY AND APPLICATIONS IN NATURAL PRODUCT SYNTHESIS

Introduction

Early Relay Metathesis Discoveries

Examples of Relay Metathesis Directed at Targets Other tan Natural Products

Examples of Relay Metathesis Motivated by Natural Product Synthesis

Examples of Relay Metatheses Thwarted in Achieving the Desired Outcome

Conclusion

CROSS-METATHESIS IN NATURAL PRODUCT SYNTHESIS

Introduction

Functionalization of Olefins

Appending a Side Chain

Couplings

Cascade Processes Involving CM

Ene-Yne CM

Alkyne CM

Conclusion and Perspectives

CASCADE METATHESIS IN NATURAL PRODUCT SYNTHESIS

Introduction

RCM-CM Sequences

Ene-Yne-Ene RCM-RCM

ROM-CM Sequences

RCM-ROM Sequences - Ring-Rearrangement Metathesis (RRM)

RCM-ROM Sequences Combined with Other Metathesis Reactions

Conclusions and Outlook

CATALYTIC ENANTIOSELECTIVE OLEFIN METATHESIS AND NATURAL PRODUCT SYNTHESIS

Introduction

Total Synthesis of Natural Products with Enantiomerically Pure Chiral Olefin Metathesis Catalysts Bearing a C2-Symmetric Diolate Ligand

Enantioselective Synthesis of Quebrachamine through an Exceptionally Challenging RCM Reaction

Synthesis of Baconipyrone C by Ru-Catalyzed Enantioselective ROCM

Conclusions and Future Outlook

METATHESIS REACTIONS IN SOLID-PHASE ORGANIC SYNTHESIS

Introduction

Metathesis-Based Cyclorelease Reaction

Ring-Closing Metathesis (RCM)

Intraresin Dimerization

Restricting Peptide Conformation through Cyclization

Cross-Metathesis on Solid Phase

Ene-Yne Metathesis on Solid Phase

Conclusion

Über Autor(innen)

Janine Cossy graduated from the University of Reims. After a postdoctoral stay with Barry Trost (1980-1982) at the University of Wisconsin, she returned to Reims where she became Director of Research of the CNRS in 1990. In the same year she moved to Paris to become Professor of Organic Chemistry at the ESPCI (Ecole Supérieure de Physique et de Chimie Industrielles de la Ville de Paris). She has published more than 330 articles and 12 patents in the field of synthetic organic chemistry and natural product synthesis. She is Associate Editor at Organic Letters since 2005.

 

Stellios Arseniyadis completed his PhD in 2002 under the guidance of Dr. C. Mioskowski at the Université Louis Pasteur (Strasbourg, France). He then joined the Research & Innovation team at Rhodia Chirex (Boston, USA) to work on the development of palladium-catalyzed coupling reactions. In 2003, he began a postdoc with Professor A.C. Spivey at Imperial College (London, UK) and, in 2004, joined Professor K.C. Nicolaou?s group at The Scripps Research Institute (La Jolla, USA).

In 2005, he was appointed a permanent CNRS researcher position in the group of Professor Cossy. His research interests include the development of new methods in the field of asymmetric catalysis and their application to the total synthesis of natural products.

 

Christophe Meyer graduated from the Ecole Nationale Supérieure de Chimie de Paris in 1991 and received his PhD from University Pierre et Marie Curie (Paris) in 1994 under the supervision of Professor J.-F. Normant and Doctor I. Marek. After a postdoctoral stay at the University of Toronto (Canada) in the laboratory of Professor M. Lautens, he was appointed a CNRS researcher position in 1996 in the group of Professor J. Cossy (ESPCI) and became Director of Research in 2008. His research focuses on the development of synthetic methodologies and total synthesis of natural products.