Beilstein J. Org. Chem.2021,17, 334–342, doi:10.3762/bjoc.17.31
operations overall from methyl N-Boc-prolinate. The key step proceeds in each case via N,O-diacylation, then selective oxidative hydrolysis of the intermediate bicyclic pyrrole and establishes a precedent for the synthesis of related C(7a)-hydroxylated pyrrolizidines.
Keywords: acyloxypyrroles; bacterial
α-haloketones, is well known [36][37]. The halogen-mediated oxidation of 3-acyloxypyrroles and related compounds, to give α-hydroxy-3-ketopyrroles, is not reported but oxidations that represent equivalent reactivity have been reported [38][39][40][41].
The concept was tested in an NMR experiment in
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Graphical Abstract
Figure 1:
The clazamycins, and selected bacterial pyrrolizidines of the vinylogous urea type. For consistency...