All the latest tools needed to plan and perform the synthesis
of complex bioactive molecules
Focusing on organic, organometallic, and bio-oriented processes,
this book explores the impact and use of the latest synthetic tools
for the synthesis of complex biologically active compounds. Readers
will discover step by step how these synthetic tools have provided
new, elegant solutions to many synthetic puzzles. Moreover, they
will discover innovative methods that make it possible to control
the exact connectivity of atoms within a molecule in order to set
precise three-dimensional arrangements.
Modern Tools for the Synthesis of Complex Bioactive
Molecules features sixteen chapters, each one written by one or
more leading experts in organic synthesis from around the world. It
covers a broad range of topics that enable readers to take
advantage of the latest methods for synthesizing complex molecules,
including:
* Modern catalysis, emphasizing key transformations such as C-H
functionalizations, cross-couplings, gold-catalyzed reactions,
metathesis-based syntheses, and asymmetric organocatalysis
* Eco-compatible transformations, including rearrangements and
domino reactions
* Tools for the synthesis of carbohydrates and alkaloids
* New techniques, including the use of fluorous tags and
engineered biosynthesis
The last two chapters explore target- and diversity-oriented
organic synthesis as well as the use of DNA-based asymmetric
catalysis, which are all promising tools for the successful
synthesis of complex bioactive molecules.
Modern Tools for the Synthesis of Complex Bioactive
Molecules is ideal for students and researchers who need to
plan and perform the synthesis of complex molecules as efficiently
as possible. The book’s expert advice will help these readers
quickly resolve a broad range of problems that can arise in organic
syntheses.
Table of Content
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, Benoy^t 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
About the author
JANINE COSSY graduated from the University of Reims
working under the supervision of Prof. Jean-Pierre Pète. 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
Supérieure de Physique et de Chimie Industrielles de la Ville
de Paris (ESPCI Paris Tech). 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 Université Paris XI and received his
Ph D in 2002 from the Université Louis Pasteur (Strasbourg,
France) working under the guidance of Dr. Charles Mioskowski. In
2001, he joined Rhodia Chi Rex (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 Chargé 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.