Two simple pyrroles react in two simple reactions to afford a dipyrromethane analogue of the southern rim of native tetrapyrroles and their catabolites.
Density functional theory calculations of Nazarov cyclizations showed that 3-alkenyl-2-indolylmethanol and tryptophol formed binary and ternary complexes, respectively, in the presence and absence of H2O to produce C–N and C–C products.
Trifluoromethylthio-promoted Nazarov cyclization of α-SCF3-vinyl (hetero)aryl ketones affords α-SCF3-substituted cyclopentenone-fused polycycles. DFT calculations further reveal the SCF3-promoting effect.
Phyllobilins – important natural products derived from chlorophylls – contain a characteristic conjugation in the southern rim, which is mimicked here in a synthetic analogue.
A one-pot Nazarov cyclization/oxidative 1,2-carbon rearrangement/Ritter reaction has been explored for the synthesis of the unprecedented 2,3-disubstituted-5-quaternary-4-amidocyclopent-2-enone and 2-quaternary-3-amidoindanones.