Quinones as Dienophiles in the Diels-Alder Reaction: History and Applications in Total Synthesis

Nawrat, Christopher C.; Moody, Christopher J.

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.

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), 2056-2077. https://doi.org/10.1002/anie.201305908

• Journal Article Type: Article
• Online Publication Date: Jan 20, 2014
• Publication Date: Feb 17, 2014
• Deposit Date: Jul 30, 2014
• Publicly Available Date: Jul 30, 2014
• Journal: Angewandte Chemie International Edition
• Print ISSN: 1433-7851
• Electronic ISSN: 1521-3773
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 53
• Issue: 8
• Pages: 2056-2077
• DOI: https://doi.org/10.1002/anie.201305908
• Keywords: Diels–Alder reaction; natural products; organic synthesis; quinones
• Public URL: https://nottingham-repository.worktribe.com/output/723279
• Publisher URL: http://onlinelibrary.wiley.com/doi/10.1002/anie.201305908/abstract
• 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
• Contract Date: Jul 30, 2014