The Diels--Alder reaction in total synthesis.
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 facilitating complex molecule construction, the Diels-Alder cycloaddition has afforded numerous and unparalleled 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.
Nicolaou
K C
KC
Department of Chemistry, The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA. kcn@scripps.edu
Snyder
Scott A
SA
Montagnon
Tamsyn
T
Vassilikogiannakis
Georgios
G
D002384:Catalysis; D002625:Chemistry, Organic / Q000266:history / Q000379:methods*; D049673:History, 20th Century; D008956:Models, Chemical; D009613:Nobel Prize; D009930:Organic Chemicals / Q000138:chemical synthesis; D013237:Stereoisomerism
D009930:Organic Chemicals