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Quinones as dienophiles in the Diels-Alder reaction: history and applications in total synthesis

Nawrat, Christopher C.; Moody, Christopher J.

Authors

Christopher C. Nawrat

Christopher J. Moody

Abstract

In the canon of reactions available to the organic chemist engaged in total synthesis, the Diels–Alder reaction is among the most powerful and well understood. Its ability to rapidly generate molecular complexity through the simultaneous formation of two carboncarbon bonds is almost unrivalled, and this is reflected in the great number of reported applications of this reaction. Historically, the use of quinones as dienophiles is highly significant, being the very first example investigated by Diels and Alder. Herein, we review the application of the Diels–Alder reaction of quinones in the total synthesis of natural products. The highlighted examples span some 60 years from the landmark syntheses of morphine (1952) and reserpine (1956) by Gates and Woodward, respectively, through to the present day examples, such as the tetracyclines.

Journal Article Type Article
Publication Date Feb 11, 2014
Journal Angewandte Chemie International Edition
Print ISSN 1433-7851
Electronic ISSN 1433-7851
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 53
Issue 8
Institution Citation Nawrat, C. C., & Moody, C. J. (2014). Quinones as dienophiles in the Diels-Alder reaction: history and applications in total synthesis. Angewandte Chemie International Edition, 53(8), doi:10.1002/anie.201305908
DOI https://doi.org/10.1002/anie.201305908
Keywords Diels–Alder reaction; natural products; organic synthesis; quinones
Publisher URL http://onlinelibrary.wiley.com/doi/10.1002/anie.201305908/abstract
Copyright Statement Copyright information regarding this work can be found at the following address: http://eprints.nottingh.../end_user_agreement.pdf
Additional Information This is the accepted version of the following article: Nawrat, C.C. & Moody, C.J., Quinones as dienophiles in the Diels-Alder reaction: history and applications in total synthesis, Angewandte Chemie International Edition, 53(8), (2014), 2056-2077, doi: 10.1002/anie.201305908, which has been published in final form at: http://onlinelibrary.wi...anie.201305908/abstract

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