Metathesis in Natural Product Synthesis: Strategies, Substrates and Catalysts

Emphasizing the impact of metathesis in natural product synthesis through the different types of key reactions, this is a comprehensive view of a hot topic. Written by top international authors, this ready reference is clearly structured and packed with important information, including representative experimental procedures for practical applications. A real must-have for anyone working in natural product synthesis.

Table of Contents:
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

About the Author :
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 Superieure 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 Universite 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 Superieure 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.