Solid-Supported Cyclotrimerization Reactions Alexander Deiters North Carolina State University, Department of Chemistry, Raleigh, NC 27695 Substantial advances have been made in the application of microwave-mediated [2+2+2] cyclotrimerization reactions in the synthesis of biologically relevant structures, natural products, and fluorophore arrays.
Phenanthridine Synthesis via [2+2+2] Cyclotrimerization Reactions A Cyclotrimerization Route to Cannabinoids
R4
R1
R3
R4
2 steps
+ N Ac
R1
R2
R2
R1 OH
R3
R2
R3 4
R
N H3C
O
via [2+2+2] cyclotrimerization
CH3 CH3
A General Approach to Triphenylenes and Azatriphenylenes: Total Synthesis of Dehydrotylophorine and Tylophorine OCH3
OCH3
H3CO
H3CO
N H3CO
H3CO OCH3
OCH3
dehydrotylophorine
Example of a Total Synthesis Enabled by a Microwave-mediated [2+2+2] Cyclotrimerization Reaction CO2H H3C
CO2Et
H3C
CO2Et
N
tylophorine
Synthesis of Anthracene and Azaanthracene Fluorophores via [2+2+2] Cyclotrimerization Reactions 2 steps
X
X = N, CH, CR
+
H3C N
H3C OCH3 illudinine
R
R
X fluorescent
