Terpenoid chemistry

As indicated before. Scheme 13.1 shows only a summary of the most important commercial chemical pathways based on the pinenes in turpentine. Terpenoid chemistry is very well developed and a lot more monoterpenes can be synthesised using one of the chemicals in Scheme 13.1 as the starting material. 

Sell CS (2003) A fragrant introduction to terpenoid chemistry. Royal Society of Chemistry, Cambridge... 

Studies of terpenoid chemistry have also in volved syntheses. Several of the complex sesquiterpenoid structures have been confirmed or. in some cases, correctly established through synthesis. Many elegant new general synthetic methods have been developed asaresult of attempts to synthesize terpenoids. The chemistry of terpenoids present a continually growing area of chemical research, perhaps the equal of any in complexity, subtlety, and variety. 

There have been a couple of reports of the presence of alkaloids in the family, blit these have not been characterized nor do they make a significant contribution to the otherwise terpenoid chemistry of the family. 

Coll, J. C., Bowden, B. F., Tapiolas, D. M., Willis, R. H., Djura, P., Streamer, M., and Trott, L., Studies of Australian soft corals-XXXV the terpenoid chemistry of soft corals and its implications, Tetrahedron, 41, 1085, 1985. 

StUle conpling to organic synthesis is the preparation of polyconjngated systems via the vinyl-vinyl conpling reactions. This methodology was nsed in carbohydrate chemistry terpenoids chemistry and in preparing polyconjngated dienes . ... 

Ch. S. Sell, A Fragrant Introduction into Terpenoid Chemistry, The Royal Society of Chemistry, Cambridge 2003. 

Terpenoids are defined as materials which are made up of isoprene (2-methylbuta-1,3-diene) units. More detail on terpenoid chemistry can be found in the book by Sell (2003). Strictly speaking, the word terpene is used to describe terpenoid hydrocarbons. In the perfumery industry, it... 

C.S. Sell, A Fragrant Introduction to Terpenoid Chemistry, Royal Society of Chemistry, Cambridge, 2003, ISBN 0-85404-681-X. Terpenoids and Steroids, Royal Society of Chemistry, Cambridge, annual review series, now incorporated into Natural Product... 

In terpenoid chemistry, the Wharton reaction of epoxyketone 30 provided an expedient entry to allylic alcohol 31, which was an intermediate toward scyphostatin, a natural product.17... 

As mentioned previously, the Chugaev elimination has found particular use in the field of terpenoid chemistry, not only in structural studies, but also in synthesis. For example, a tandem Claisen rearrangement-ene reaction of geraniol derivative 23 gave... 

Laboratory of Terpenoid Chemistry, Institute of Chemistry, the Academy of Sciences of Moldova, Academiei Str. 3, Chisinau, MD-2028, the Republic of Moldova... 

The major producers of the rose alcohols and citral have become so for a variety of reasons. Companies which manufacture wood and paper products produce sulfate turpentine or similar by-products rich in pinenes. They, or their subsidiaries, may then produce terpenoid fragrance materials from pinenes as a way of generating income from their by-product. Pharmaceutical companies which manufacture vitamins use terpenoid intermediates and so will often diversify into the manufacture of aroma chemicals. Their basic feedstocks are likely to be of petrochemical origin. Similarly, manufacturers of synthetic rubber possess technology for the use of isoprene as a feedstock and so are also likely to diversify into terpene aroma chemical manufacture. Fragrance companies will develop a position in terpenoid chemistry because of the importance of terpenoids as ingredients. 

Ideal as both an introduction to terpenoid chemistry and as a refresher course, A Fragrant Introduction to Terpenoid Chemistry, with its real-life problems and appreciation of the relevance of chemistry to everyday life, will prove invaluable to students, lecturers and industrialists alike. 

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 author s 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. 

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... 

---