The Total Synthesis of Natural Products, Part B: Bicyclic and Tricyclic Sesquiterpenes / Edition 1

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The past two decades have seen an explosion in research on the synthesis of sesquiterpenes, an important class of hydrocarbons commonly found in oils, resins, and balsams. Volume Eleven in The Total Synthesis of Natural Products series continues to review this dynamic area of chemistry. It features systematic, A-to-Z coverage of sesquiterpenes synthesized between 1979-1994-a sesquidecade.

Focusing on bicyclic and tricyclic compounds in sesquiterpene synthesis, this authoritative work complements Volume Ten's coverage of acyclic and monocyclic sesquiterpenes. The authors comb through the hundreds of sesquiterpene syntheses already developed, consolidating the multitude of research papers, and providing extensive references as well as author and subject indexes. To keep the presentation manageable, they emphasize literature where natural products were prepared, leaving out natural ring systems or compounds whose structures were misassigned.

This volume presents multiple syntheses of the same compound in chronological order, making the various steps of the synthetic strategy easily accessible. In addition, it addresses one of the most important developments in sesquiterpene research, namely the increase in compound targets prepared in an optically active form. And while syntheses of racemates are not specifically marked, legends for synthesis schemes producing optically active compounds include their absolute configurations, signs of optical rotation, or both.

An important resource for organic chemists, pharmaceutical and medicinal chemists, natural prod-ucts chemists, and biochemists, The Total Synthesis of Natural Products offers valuable insight into the structure and makeup of sesquiterpenes while serving as a practical tool for locating any of the major classes of sesquiterpene compounds.

An invaluable guide for the chemist interested in natural products.

Providing a fascinating, comprehensive look at sesquiterpene synthesis, Volume Eleven of The Total Synthesis of Natural Products reviews sesquiterpenes synthesized in the period 1979-1994, continuing the coverage begun with Volume Ten in the series (see below). This authoritative work:
* Focuses on bicyclic and tricyclic sesquiterpenes.
* Explains the structure and makeup of this important class of hydrocarbons.
* Serves as a useful, practical tool for researchers interested in locating any of the major classes of sesquiterpene compounds.
* Provides multiple syntheses of the same compound chronologically, clearly showing the evolution of the synthetic strategy.

Also available . . .THE TOTAL SYNTHESIS OF NATURAL PRODUCTS Volume Ten, Edited by David Goldsmith.

A complement to this work, Volume Ten examines compounds with acyclic and monocyclic ring structures in sesquiterpene synthesis. 1997 (0-471-59679-5) 173 pp.

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Product Details

  • ISBN-13: 9780471188742
  • Publisher: Wiley
  • Publication date: 5/26/1999
  • Series: Total Synthesis of Natural Products Series , #11
  • Edition description: Volume 11
  • Edition number: 1
  • Pages: 480
  • Product dimensions: 6.30 (w) x 9.37 (h) x 1.24 (d)

Meet the Author

DAVID GOLDSMITH, PhD, is Pro- fessor of Chemistry at Emory University in Atlanta, Georgia. He is former Chair of the Emory Chemistry Department and has been Visiting Professor at Stras-bourg, Mulhouse, and Grenoble. Professor Goldsmith received his PhD in organic chemistry from Columbia University. His research interests have been principally in the field of natural product synthesis.

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Table of Contents






Miscellaneous Hydronaphthalenes.

Fused Ring Compounds: 6,3.

Fused Ring Compounds: 6,5.

Fused Ring Compounds: 6,7.

Fused Ring Compounds: 6,8.

Fused Ring Compounds: 5,7.

Fused Ring Compounds: 5,8.

Fused Ring Compounds: 4,9.

Fused Ring Compounds: 5,5.

Isolated Rings.

Spirocyclic Systems.

Bridged Systems.


Angular Triquinanes.


Linear Triquinanes.

Miscellaneous Fused Tricyclic Sesquiterpenes.

Bridged Tricyclic Sesquiterpenes.




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