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2014 ; 12
(38
): 7445-68
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Nitroso Diels-Alder (NDA) reaction as an efficient tool for the functionalization
of diene-containing natural products
#MMPMID25119424
Carosso S
; Miller MJ
Org Biomol Chem
2014[Oct]; 12
(38
): 7445-68
PMID25119424
show ga
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.