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The Diels-Alder Reaction in Total Synthesis

'The Diels-Alder Reaction in Total Synthesis'
1. Introduction After numerous near-discoveries of the [4?2] cycloaddition reaction by several luminaries in the field of organic chemistry during the early part of the 20th century,[1, 2]the keen insight of Professor Otto Diels[3]and his student, Kurt Alder,[4]in properly identifying the products (4 and 6, Scheme 1) arising from the reaction of cyclopentadiene (1) with quinone (2) denotes a historic event in the field of chemistry for which these two individuals were rewarded with a reaction that would henceforth bear their names.[5]With prophetic fore- sight, Diels and Alder clearly anticipated the importance of this discovery in their landmark 1928 paper, particularly as applied to natural product synthesis, through the following remark: ?Thus it appears to us that the possibility of synthesis of complex compounds related to or identical with natural products such as terpenes, sesquiterpenes, perhaps even alkaloids, has been moved to the near prospect.∫ However, in an intriguing moment of scientific territoriality, which might appear slightly off-color or even amusing to a contem- Scheme 1. The discovery of the Diels±Alder reaction in 1928, a reaction for which the namesakes would receive the Nobel Prize in Chemistry in 1950: Diels the professor, Alder the student.[5] porary audience, the authors issued the following ominous warning to those researchers interested in applying their discovery to total synthesis: ?We explicitly reserve for ourselves the application of the reaction developed by us to the solution of such problems.∫[2] The Diels±Alder Reaction in Total Synthesis K. C. Nicolaou,* Scott A. Snyder, Tamsyn Montagnon, and Georgios Vassilikogiannakis The Diels±Alder reaction has both enabled and shaped the art and science of total synthesis over the last few decades to an extent which, arguably, has yet to be eclipsed by any other transformation in the current synthetic repertoire. With myriad applications of this magnificent pericyclic reaction, often as a crucial element in elegant and programmed cascade sequences facilitatingcomplexmoleculecon- struction, the Diels±Alder cycloaddi- tion has afforded numerous and un- paralleled solutions to a diverse range of synthetic puzzles provided by nature in the form of natural products. In celebration of the 100th anniversary of Alder×s birth, selected examples of the awesome power of the reaction he helped to discover are discussed in this review in the context of total synthesis to illustrate its overall versatility and underscore its vast potential which has yet to be fully realized. Keywords:biomimetic synthesis¥ cycloaddition¥Diels±Alder reaction ¥ molecular diversity ¥ total synthesis [*] Prof. Dr. K. C. Nicolaou, S. A. Snyder, Dr. T. Montagnon, Dr. G. Vassilikogiannakis Department of Chemistry and The Skaggs Institute for Chemical Biology The Scripps Research Institute 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA) Fax: (?1)858-784-2469 E-mail: kcn@scripps.edu and Department o
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