Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 15, 2017
Previous Article Next Article

Application of the aza-Diels–Alder reaction in the synthesis of natural products

Author affiliations

Abstract

The Diels–Alder reaction that involves a nitrogen atom in the diene or dienophile is termed the aza-Diels–Alder reaction. As well as the powerful all-carbon Diels–Alder reaction, the aza-Diels–Alder reaction has also played an important role in the total synthesis of natural products. Herein, we review various natural products using an aza-Diels–Alder reaction as a key step to their total synthesis, and divide the syntheses into inter- and intra-molecular aza-Diels–Alder reactions and a retro-aza-Diels–Alder reaction. Inter- and intra-molecular aza-Diels–Alder reactions involve an imine as an electron deficient dienophile and an imine as an electron deficient azadiene. The significance of the aza-Diels–Alder reaction for the construction of a six-membered ring containing nitrogen is tremendous, but the development of asymmetric, in particular catalytic enantioselective intramolecular aza-Diels–Alder reaction in the total synthesis of natural products remains highly challenging, and will no doubt see enormous advances in the future.

Graphical abstract: Application of the aza-Diels–Alder reaction in the synthesis of natural products

Back to tab navigation

Article information


Submitted
19 Dec 2016
Accepted
06 Mar 2017
First published
06 Mar 2017

Org. Biomol. Chem., 2017,15, 3105-3129
Article type
Review Article

Application of the aza-Diels–Alder reaction in the synthesis of natural products

M. Cao, N. J. Green and S. Xu, Org. Biomol. Chem., 2017, 15, 3105
DOI: 10.1039/C6OB02761J

Social activity

Search articles by author

Spotlight

Advertisements