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The Organic Chemistry of Sugars. Edited by Daniel E. Levy and Pter Fgedi

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Angewandte
Books
Chemie
Six-Membered Hetarenes with
One Nitrogen or Phosphorus Atom
Science of Synthesis, Vol. 1. Edited by
D. St. C. Black.
Georg Thieme
Verlag, Stuttgart
2005. 1320 pp.,
hardcover
E 2000.00.—ISBN
3-13-118651-9
This book is Volume 15 of 48 volumes of
the new Houben–Weyl collection Science of Synthesis. This collection, which
will be completed in the next few years,
is divided into six categories. More
information on the whole series and
some opinions of reviewers can be found
on the web site http://www.science-ofsynthesis.com/index.shtml. Volume 15
belongs to Category 2 (Volumes 9–17),
which is devoted to hetarenes, and
covers the synthesis of heterocyclic
compounds. The major part concerns
methods for the synthesis of pyridines
and their derivatives (pyridine 1-oxide,
pyridinium salts) as well as pyridinones,
quinolines and quinolinones, isoquinolines and isoquinolinones, naphthyridines, acridines, and phenanthridines.
The aim of this part (1096 pp.) is to
present the state of the art concerning
the synthesis of this venerable class of
compounds, so important in synthetic
and medicinal chemistry. A much
shorter part (93 pp.) concerns the more
recent and less developed class of hetarenes with one P atom and is intended to
help future research in this particular
field, visibly still in its infancy.
The Houben–Weyl series, since its
beginning (almost one century!), conAngew. Chem. Int. Ed. 2006, 45, 3399 – 3400
stitutes a well-known series of textbooks
on organic synthesis. Originally the
ambition was to cover, as far as possible,
all aspects of organic synthesis. In doing
so, it effectively became a sort of bible in
the field; but times have now changed!
The enormous amount of literature now
available defies such a task, which is
now increasingly assumed by databases
such as Beilstein or SciFinder. These
databases are of incomparable value
when one wants to find a rather welldefined product or reaction. However, if
one wants general approaches for the
synthesis of species such as pyridines,
one will be faced with hundreds of
thousands of results and a prohibitive
quantity of work to analyze them. Thus,
there is a need for comprehensive
reviews covering such topics of broad
interest. This is the laudable goal of the
series Science of Synthesis.
The chapter classification of synthetic methods for a particular class of
molecules follows the traditional
Houben–Weyl numbering system. It is,
in my opinion, a valuable classification,
but quite difficult to comprehend. It is
indeed difficult to understand where
you are when, opening a page, you are
faced with a paragraph number such as
15.3.1.1.1.3.3.1.2.! Nevertheless, as compensation for that, it has the great
advantage of introducing a logical
system into a very complex situation,
such as the analysis of all methods now
available for the synthesis of pyridines.
The presentation of the different
approaches to the synthesis of compound subclasses of nitrogen and phosphorus six-membered heterocycles is
first divided into several categories,
such as ring-closure reactions, ring transformations, substituent modifications,
etc. Under these categories are then
presented
the
different
general
approaches and, for each one, different
methods and their variations. A typical
experimental procedure is always
described at the end. The examples
illustrating a strategy are not necessarily
the most relevant, but they are always
well chosen for a good understanding.
For example, methods for the syntheses
of pyridines and pyridinium salts, which
are very similar, have been separated,
whereas they could have been joined
together. Examples in chiral series are
also rare or absent. I particularly appre-
ciated the classification used for ringclosure reactions. In the case of the
synthesis of pyridines, for example, the
classification is based on the number of
C C and C N bonds formed, followed
by the number and nature of fragments
used. This is particularly important in
view of the complex situation in this
field, which generally uses empirical
parameters (reaction name, type of
reagent or reaction, etc.). This is also
very useful for evaluating the merits of a
particular approach, for example with
regard to its convergence or its possible
use in multicomponent approaches.
This Volume 15 of Science of Synthesis is of considerable value for anyone
involved in the synthesis of the class of
substances covered. I received this
volume when I was trying to evaluate
new results concerning pyridine synthesis. The task was turning out to be very
difficult, because of scattered data and a
lack of comprehensive and up-to-date
literature. This book was exactly what I
needed for this purpose, and I think that
the authors are to be thanked for their
large contribution of high-quality work.
Christian Marazano
Institut de Chimie des Substances
Naturelles
Gif-sur-Yvette (France)
The Organic Chemistry of Sugars
Edited by Daniel E.
Levy and Pter
Fgedi. CRC Press/
Taylor & Francis,
Boca Raton 2006.
928 pp., hardcover
$ 199.95.—ISBN
0-8247-5355-0
Compared with many other organic
molecules, the special quality of carbohydrates, which are known to play a key
role in many biological processes, is
their high density of functional groups
and their impact on each other. As a
6 2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
3399
Books
consequence, sugars that apparently
differ only slightly (e.g., in the configuration of a single center of chirality)
often display a fundamentally different
reactivity pattern. The transferability of
reactivities, a common concept in
organic chemistry, is therefore more
complicated. This is probably the
reason why carbohydrate chemistry is
often regarded as a specialty, and is
treated only superficially in textbooks
and lectures on organic chemistry. The
aim of this book edited by Levy and
F>gedi is to oppose that perception. It
consists of 4 parts with 16 chapters in
total. Each chapter starts with an introduction that allows nonspecialists to also
find a way of approaching the subject.
Particularly successful in this respect is
the first part, which has a strong textbook character. The contributions, all
written all by well-known researchers,
are well coordinated with each other
and cover most aspects of synthetic
sugar chemistry.
In the first part, comprising five
chapters, basic aspects regarding structure and reactivity of carbohydrates are
treated. Chapter 1 ends with a survey of
the history of carbohydrate chemistry,
from Emil Fischer to the beginning of
the 21st century. The second chapter is
about constitution, configuration, and
conformation of monosaccharides and
some oligosaccharides. All the important concepts, including the anomeric
and exo-anomeric effects, as well as
nomenclature of oligosaccharides, are
presented. Chapter 3 concerns the dayto-day business of the carbohydrate
chemist, the manipulation of protecting
groups. Given the fact that these operations consume a considerable amount
of laboratory time, the chapter could
have been a bit longer. Of course, there
are many reviews on that topic, which
are cited here. Nevertheless, at this point
I would have preferred more examples
and mechanistic explanations of the
regioselectivities described. On the
other hand, all the important principles
are considered, and many protecting
3400
www.angewandte.org
group strategies from the recent literature are mentioned. Also, the comparison of different total syntheses of
trimeric Lewisx with regard to the protecting group strategy chosen is worth
reading. Glycosylation methods are the
subject of the following chapter, which
has the highest number (640) of literature references within the book. All the
relevant methods are described in a
systematic way. Stereochemical aspects
of glycosylations are discussed on an
appropriate level. The numerous tables
that allow easy access to hundreds of
original publications on the use of all
kinds of activators for specific types of
glycosyl donors are very helpful, especially for a synthetic chemist. The first
part of the book ends with a chapter on
oligosaccharide synthesis. Different
strategies for the assembly of these
natural products, even including onepot sequential glycosylations and automated solid-phase syntheses, are described.
The second part, consisting of four
chapters, covers the conversion of carbohydrates into molecules that lack
some of the features that define carbohydrates. In Chapter 6 the reader is
introduced to reactions for the functionalization of sugars. Besides substitutions
and eliminations, the chapter discusses
C C bond-forming reactions, redox
reactions, and rearrangements. This is
followed by chapters on the synthesis of
C-glycosides, carbasugars, and sugars
with endocyclic heteroatoms other than
oxygen.
The application of sugars as tools in
organic chemistry is the subject of the
third part, which comprises four chapters. Chapter 10 summarizes recently
published work on the use of sugars as
chiral auxiliaries. That is followed by a
detailed discussion of their exploitation
as chiral-pool materials for the synthesis
of enantiomerically pure complex target
molecules. Continuing this approach,
Chapter 12 concerns the syntheses of
carbohydrate-containing natural products. This part ends with an overview of
6 2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
the latest developments (including publications up to 2005) in the area of
asymmetric de novo synthesis of monosaccharides and related molecules.
In the last part, comprising three
chapters, several recent developments in
the glycosciences are considered. Combinatorial carbohydrate chemistry is the
subject of Chapter 14. Unfortunately,
recent work on carbohydrate arrays is
left out. Chapter 15 deals with the
preparation of glycopeptides in solution
and on a solid phase, with the main
emphasis on O-glycosidic structures.
Unfortunately, the application of ligation reactions for the synthesis of larger
glycoproteins is mentioned only briefly.
The book ends with a nice overview of
the use of carbohydrate mimetics as
therapeutics. Using several examples,
including the antiviral tamiflu, about
which there has been much public discussion recently, the ups and downs on
the way towards sugar-based drugs are
illustrated.
The more than 3000 references that
are cited could certainly have been
slightly more up-to-date. In general,
the literature coverage extends to 2002/
2003. The only exception to that is the
chapter on C-glycoside synthesis, which
fails to cover the developments of the
last ten years. In an exemplary manner,
all the references include the titles in
addition to the authors. This makes it
easier for the reader to decide if a
particular article is worth reading. The
content of the book is easily accessible
through the detailed table of contents as
well as the index. I found only a few
typographical errors. All in all, the book
is highly recommended for carbohydrate chemists and those wishing to
become one.
Valentin Wittmann
Fachbereich Chemie
Universit<t Konstanz (Germany)
DOI: 10.1002/anie.200685377
Angew. Chem. Int. Ed. 2006, 45, 3399 – 3400
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