Modern Tools for the Synthesis of Complex Bioactive Molecules

JANINE COSSY graduated from the University of Reims working under the supervision of Prof. Jean-Pierre Pete. After a postdoctoral stay with Prof. Barry Trost (1980-1982) at the University of Wisconsin, she returned to Reims where she became Director of Research of the CNRS in 1990. The same year, she moved to Paris to become Professor of Organic Chemistry at the Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI ParisTech). She has published over 380 articles and filed thirteen patents in the field of synthetic organic chemistry and natural product synthesis. She is Associate Editor at Organic Letters since 2005. STELLIOS ARSENIYADIS was born in Greece in 1975. He studied chemistry at the Universite Paris XI and received his PhD in 2002 from the Universite Louis Pasteur (Strasbourg, France) working under the guidance of Dr. Charles Mioskowski. In 2001, he joined Rhodia ChiRex (Boston, USA) for an eighteen-month internship in collaboration with Prof. Stephen L. Buchwald (MIT, USA). He then spent a year as a postdoctoral fellow at Imperial College London (UK) working under the supervision of Prof. Alan C. Spivey, after which he joined Prof. K. C. Nicolaou's group at The Scripps Research Institute (La Jolla, USA) for an additional postdoc. In 2005, he was appointed by the CNRS as Charge de Recherche in Prof. Janine Cossy's group. His research interests include the development of new synthetic tools and their application to the total synthesis of complex natural products.

FOREWORD vii PREFACE ix CONTRIBUTORS xi CHAPTER 1 C--H FUNCTIONALIZATION: A NEW STRATEGY FOR THE SYNTHESIS OF BIOLOGICALLY ACTIVE NATURAL PRODUCTS 1 Sophie Rousseaux, Benoyt Lie'gault, and Keith Fagnou CHAPTER 2 THE NEGISHI CROSS-COUPLING IN THE SYNTHESIS OF NATURAL PRODUCTS AND BIOACTIVE MOLECULES 33 Evelina Colacino, Jean Martinez, and Fre'de'ric Lamaty CHAPTER 3 METAL-CATALYZED C--HETEROATOM CROSS-COUPLING REACTIONS 77 Renata Marcia de Figueiredo, Jean Marc Campagne, and Damien Prim CHAPTER 4 GOLDEN OPPORTUNITIES IN THE SYNTHESIS OF NATURAL PRODUCTS AND BIOLOGICALLY ACTIVE COMPOUNDS 111 Fabien Gagosz CHAPTER 5 METATHESIS-BASED SYNTHESIS OF COMPLEX BIOACTIVES 155 Jean-Alexandre Richard, Sin Yee Ng, and David Y.-K. Chen CHAPTER 6 ENANTIOSELECTIVE ORGANOCATALYSIS: A POWERFUL TOOL FOR THE SYNTHESIS OF BIOACTIVE MOLECULES 189 Mitsuru Shoji and Yujiro Hayashi CHAPTER 7 ASYMMETRIC PHASE-TRANSFER CATALYSIS 213 Seiji Shirakawa, Shin A. Moteki, and Keiji Maruoka CHAPTER 8 REARRANGEMENTS IN NATURAL PRODUCT SYNTHESIS 243 Jose' Marco-Contelles and Elena Soriano CHAPTER 9 DOMINO REACTIONS IN THE ENANTIOSELECTIVE SYNTHESIS OF BIOACTIVE NATURAL PRODUCTS 271 Lutz F. Tietze, Scott G. Stewart, and Alexander Du¨fert CHAPTER 10 FLUOROUS LINKER-FACILITATED SYNTHESIS OF BIOLOGICALLY INTERESTING MOLECULES 335 Wei Zhang CHAPTER 11 THE EVOLUTION OF IMMOBILIZED REAGENTS AND THEIR APPLICATION IN FLOW CHEMISTRY FOR THE SYNTHESIS OF NATURAL PRODUCTS AND PHARMACEUTICAL COMPOUNDS 359 Rebecca M. Myers, Kimberley A. Roper, Ian R. Baxendale, and Steven V. Ley CHAPTER 12 SYNTHETIC APPROACHES TO BIOACTIVE CARBOHYDRATES 395 Xavier Guinchard, Se'bastien Picard, and David Crich CHAPTER 13 AMMONIUM YLIDES AS BUILDING BLOCKS FOR ALKALOID SYNTHESIS 433 Scott Bur and Albert Padwa CHAPTER 14 PRECURSOR-DIRECTED BIOSYNTHESIS OF POLYKETIDE AND NONRIBOSOMAL PEPTIDE NATURAL PRODUCTS 485 Colin J. B. Harvey and Chaitan Khosla CHAPTER 15 TARGET-ORIENTED AND DIVERSITY-ORIENTED ORGANIC SYNTHESIS 513 Raphae¨l Rodriguez CHAPTER 16 DNA AS A TOOL FOR MOLECULAR DISCOVERY 539 Michael Smietana, Jean-Jacques Vasseur, Janine Cossy, and Stellios Arseniyadis INDEX 557