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Issue 38, 2014
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Nitroso Diels–Alder (NDA) reaction as an efficient tool for the functionalization of diene-containing natural products

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Abstract

This review describes the use of nitroso Diels–Alder reactions for the functionalization of complex diene-containing natural products in order to generate libraries of compounds with potential biological activity. The application of this methodology to the structural modification of a series of natural products (thebaine, steroidal dienes, rapamycin, leucomycin, colchicine, isocolchicine and piperine) is discussed using relevant examples from the literature from 1973 onwards. The biological activity of the resulting compounds is also discussed. Additional comments are provided that evaluate the methodology as a useful tool in organic, bioorganic and medicinal chemistry.

Graphical abstract: Nitroso Diels–Alder (NDA) reaction as an efficient tool for the functionalization of diene-containing natural products

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Publication details

The article was received on 19 May 2014, accepted on 06 Aug 2014 and first published on 14 Aug 2014


Article type: Review Article
DOI: 10.1039/C4OB01033G
Citation: Org. Biomol. Chem., 2014,12, 7445-7468
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    Nitroso Diels–Alder (NDA) reaction as an efficient tool for the functionalization of diene-containing natural products

    S. Carosso and M. J. Miller, Org. Biomol. Chem., 2014, 12, 7445
    DOI: 10.1039/C4OB01033G

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