Metathesis in Natural Product Synthesis (eBook)

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.

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