Issue 38, 2014

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

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

Article information

Article type
Review Article
Submitted
19 May 2014
Accepted
06 Aug 2014
First published
14 Aug 2014

Org. Biomol. Chem., 2014,12, 7445-7468

Author version available

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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