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Issue 15, 2017
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Application of the aza-Diels–Alder reaction in the synthesis of natural products

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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

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Publication details

The article was received on 19 Dec 2016, accepted on 06 Mar 2017 and first published on 06 Mar 2017


Article type: Review Article
DOI: 10.1039/C6OB02761J
Citation: Org. Biomol. Chem., 2017,15, 3105-3129
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    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

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