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In this book, the authors raise the question "Why
do Organic Synthesis?" Now with the power of
instrumentation at the chemist's disposal, total synthesis is no longer
necessary for structure proof. So where does the future of
organic synthesis lie?
To answer this question, the authors present the
development of the problems as attacked by the synthetic
chemist. This consists of first formulation of the "Goals of an
Organic Synthesis" (Chapter 1) followed by a review of the
"Tactics of Synthesis" (Chapter 2). Here they "present merely a
step-by-step exposure of the basic guidelines that govern the
elaboration and utilization of synthetic methods as tools for
the solution of organic synthesis problems." Chapter 2
comprises almost half of the book (185 pages). It is divided into
sections that address the principle classes of transformations
required, the "tools", in the synthesis of a target molecular
structure. The process is introduced by an excellent discussion of
the difference between kinetic and thermodynamic
control events. The role of entropy is also presented. The authors
then present the available tools for (i) building
carbon-to-carbon bonds, (ii) functional group interconversions, (iii)
control of selectivity, (iv) construction of cyclic systems, (v)
carbon skeleton rearrangements.
Along the way they develop the concept of
"synthons" and elucidate the nature of "reactive equivalence" in
differing but readily interconvertable "building blocks". In this
chapter, the reader is expected to have a solid foundation in
basic organic chemistry, but from there, the authors lead the
reader to the most recent and complex transformations in the
synthetic arsenal.
Chapter 3 presents a detailed analysis of the
"Strategy of Synthesis", the importance of planning the synthetic
process. Herein are developed the concepts of "strategic
core" and "strategic bond" as keys to the planning process.
Both linear and convergent schemes are described. Special
attention is focused on the retrosynthetic approach to
synthesis design. The chapter ends with a review of contributions
and limitations of computer-aided retrosynthetic studies. It
was argued that effective planning of a synthesis required
that "anyone wishing to be involved in organic
synthesis--read, analyze, and store data from the current scientific
literature!" It was suggested that one of the principal contributions
of computer-assisted retrosynthetic analysis was the
compilation and systemization of the immense amount of information
in the area of organic synthesis.
Chapter 4 presents selected examples of the more
recent achievements in organic synthesis. These include preparation
of "exotic" structures resulting from structure-oriented
design as well as directly useful substances (e.g.,
pharmaceuticals) resulting from function-oriented design.
The last short chapter reviews the contributions of
organic synthesis to the whole of the body of scientific
knowledge. In particular, it argues the significance of model systems
in the investigation of biochemical processes.
Throughout the book, the authors repeat the theme,
organic synthesis is an overtly practical enterprise. They
support this assertion with numerous examples of useful products that
were developed either as a direct result or as a byproduct
of synthetic studies. They highlight the ability, even
necessity, of synthetic processes to prepare analogues to known
useful substances to optimize their desirable properties.
This is especially important in pharmaceutical chemistry.
A second theme, expressed in the title, is the art of
the enterprise. Certainly, the craft of organic synthesis is
based upon a broad foundation of studies in reaction processes
and mechanisms, but it also requires an artist's creativity to
perceive the relationships and processes that result in the
exquisitely elegant schemes found in recent literature. Although
serendipity is undoubtedly a frequent component, many of the
most impressive outcomes were carefully engineered to
fulfill a desired end.
The book was written with the assumption that
the reader is well founded in basic organic theory. The
authors build upon that foundation, culminating in the presentation
of the most recent advances in synthesis of both exotic and
useful substances. The reactions involved are thoroughly described
and presented in well-drawn structural presentations
(schemes). The book is well indexed and each chapter is heavily
referenced (19 pages of densely packed references, both
original papers and seminal reviews). In this respect it would be
a valuable reference for anyone in the field. I was
impressed with the multitude of developments that have occurred
in the last few decades. This compilation would serve as an
excellent review and update for organic chemists who have
not remained completely current in the field as well as an
excellent source for practitioners newly entering the field. While
I would not recommend the book as a course text, it
would provide excellent collateral reading and be an
outstanding source for course lecture material. Overall, it is very
readable and is highly recommended reading to anyone interested in
the contributions of organic synthesis to the scientific enterprise.
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