Preface

Downloaded on 31 October 2012 Published on 31 October 2007 on http://pubs.rsc.org | doi:10.1039/9781847550019-FP005

The mind is afire to be kindled, not a vessel to be filled. Plut arch

The book is aimed primarily at university undergraduates, postgraduates and professional chemists who wish to build up their knowledge of terpenoid chemistry. It is intended to serve as a general introduction to the exciting field of terpenoid chemistry. Terpenoids play an important part in all our lives, from perfumes through insect pest control to pharmaceuticals such as steroid hormones and the anti-cancer drug paclitaxel. The subject therefore also serves to illustrate the importance of chemistry in everyday life. In the interests of length and also of the authors expertise, we will concentrate on the mono- and sesquiterpenoids and primarily those of interest as fragrance ingredients. Higher terpenoids will be mentioned and the reader will be able to extrapolate the basic principles of terpenoid chemistry from the more detailed examples using lower terpenoids to these higher homologues. Chemistry is a multi-faceted discipline and each part is interconnected with every other. It is also the central natural science, lying between physics and biology. To understand chemistry we must understand something of physics. Equally, since living organisms function through chemistry, we must understand that chemistry in order to fully understand them. I have therefore included some elements of biochemistry and molecular biology in order to illustrate the key role which terpenoids play in the processes of life and the senses of sight and smell in particular. Terpenoid chemistry touches on all aspects of stereochemistry and mechanism. However, one prominent feature of terpenoid chemistry is that of carbocation reactions and the fundamental research which forms the basis of our understanding of this area, was carried out on fragrant terpenoids. Some of the most elegant of all total syntheses involve sesquiterpenoid targets. The book will therefore also serve as a refresher course on mechanism, stereochemistry and synthetic methodology. Where appropriate, basic principles are discussed in order to prepare for their application to terpenoids. For example, the elements of stereochemistry are reviewed in Chapter 4 before showing how
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Preface

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important they are in understanding the chemistry of carvone and menthol. I recommend that any student readers of this book acquire a set of molecular models. These will be particularly helpful in understanding stereochemistry and carbocation rearrangements in cyclic molecules. The first two chapters are designed to excite by showing the diversity of terpenoids and their roles in living organisms. Also amazing is that such a diversity can be produced from one simple feedstock and a handful of chemical reactions. Students going through the book from the beginning should not be put off by the apparently complex chemistry described, especially in Chapter 2. The basic principles of the chemistry are covered in detail in later chapters. There is a selection of problems involving terpenoid chemistry and this is followed by worked solutions. As always, problems are a good way of testing ones understanding of a subject and this is one of the reasons for including a number in this book. However, some of them serve a dual purpose and are almost integral parts of the text since they explain some points which are, deliberately, passed over rather superficially in the main body of the text. If the reader finds something which appears to have been glossed over, then it would be useful to check the problems section to see if the explanation lies there. There is a bibliography which will serve to direct those who wish to know more to some of the key sources of information. These are arranged by subject in order to make it easy to use. There are also specific references which are cited in the main body of the text. These are mostly to original research papers and are designed to encourage the students to test the excitement of exploring the original literature. There is a small degree of overlap between the references and the bibliography. I felt it better to accept this than to create a complex system of cross-referencing which would reduce accessibility. I believe that science and art should not be separated but should be taken together since each helps in our understanding and appreciation of the other. Many great scientists were also accomplished in the arts. For example, Albert Einstein played the violin and Alexander Borodin, besides being a professor of chemistry at a medical school in Saint Petersburg and a leading figure in research into alkaloids, was one of the greatest Russian composers of his day. Perfumery is clearly a blend of creative art and chemical science. I have therefore tried to develop a link to philosophy and the arts through the use of appropriate quotations at the start of each chapter and by the use of perfumery as an example of discovery chemistry.

Downloaded on 31 October 2012 Published on 31 October 2007 on http://pubs.rsc.org | doi:10.1039/9781847550019-FP005