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

Nawrat, Christopher C. and Moody, Christopher J. (2014) Quinones as dienophiles in the Diels-Alder reaction: history and applications in total synthesis. Angewandte Chemie International Edition, 53 (8). pp. 2056-2077. ISSN 1433-7851

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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.

Item Type: Article
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.wiley.com/doi/10.1002/anie.201305908/abstract
Keywords: Diels–Alder reaction; natural products; organic synthesis; quinones
Schools/Departments: University of Nottingham UK Campus > Faculty of Science > School of Chemistry
Depositing User: Moody, Prof Christopher
Date Deposited: 30 Jul 2014 13:27
Last Modified: 15 Sep 2016 03:53
URI: http://eprints.nottingham.ac.uk/id/eprint/3300

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