Beilstein J. Org. Chem.2021,17, 1374–1384, doi:10.3762/bjoc.17.96
.
Synthesis of imidazole and benzimidazole containing truxene derivatives 14 and 16.
Construction of truxene-based di- and trioxazole derivatives 21 and 20.
Synthesis of benzene-bridgedrings containing trioxazolotruxene system 25.
Supporting Information
Supporting Information File 174: Additional general
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Graphical Abstract
Scheme 1:
Retrosynthetic pathways to the pyrrole-based C3-symmetric truxene derivative 6.
Beilstein J. Org. Chem.2016,12, 985–999, doi:10.3762/bjoc.12.97
systems rapidly and efficiently, though additional catalyst development is needed.
Keywords: bridgedrings; carbene; cascade reaction; C–H bond insertion; nitrene; Introduction
Bridged polycyclic natural products are an inviting challenge to the synthetic chemist for their rich display of functional
construction of bridgedrings have been reported. These methods usually rely on existing functional groups to build the rings, consequently leading to the synthesis of a single isomer. To access a different isomer, either the synthetic sequence must be revised to install the key functional groups at
[31].
Metal-catalyzed reactions
Copper
The earliest example to our knowledge of transition metal catalysis for the formation of bridgedrings via C–H bond insertion was Wolff’s use of copper (Scheme 6) [32][33]. Silver was also examined as a possible catalyst, but then a Wolff rearrangement was the