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

2014/01/01 by Serena Carosso, Marvin J. Miller · 1 citation
Medicine · Chemistry · #Microbial Natural Products and Biosynthesis #Asymmetric Synthesis and Catalysis #Chemical synthesis and alkaloids

paper · doi:10.1039/c4ob01033g

openalex publication_date 2014/01/01 · openalex created_date 2025/10/10 · openalex updated_date 2026/08/04

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.

Citations

• Biochemical basis of enhanced drug bioavailability by piperine: evidence that piperine is a potent inhibitor of drug metabolism.
• Natural Products as Sources of New Drugs over the Last 25 Years
• Natural Products as Sources of New Drugs over the Period 1981−2002
• Small Molecule Natural Products in the Discovery of Therapeutic Agents: The Synthesis Connection

Cited by

• Diverted total synthesis [wikipedia]