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Beilstein J. Org. Chem. 2015, 11, 481–492, doi:10.3762/bjoc.11.54
Graphical Abstract
Scheme 1: The synthesis of N-monoallylated indigo derivatives.
Scheme 2: The synthesis of 8a-hydroxyazepinodiindolones.
Figure 1: The structure and X-ray crystal structure (ball and stick representation) of azepinodiindolone 7. T...
Figure 2: Dihydroazepino[1,2-a:3,4-b']diindolones from Nb-acyl-L-tryptophanamides [5].
Scheme 3: The optimal synthesis of spiro heterocycles 12–16, and spiro/polyfused ring heterocycles 17 and 18 ...
Scheme 4: The synthesis of the oxa-bridged azepinodiindolone 22 from indigo and 1-bromo-3-methylbut-2-ene.
Figure 3: Modelled structure (Spartan 10, v1.1.0, Wavefunction Inc) of bridged indigo-tetrahydrofuran product ...
Scheme 5: The reaction of indigo with cinnamyl bromide yielding two spiro-based derivatives.
Figure 4: Structural analysis of compound 23. Left: modelled structure showing the cisoid configuration of th...
Scheme 6: Proposed mechanism for the synthesis of the red diindolone heterocycles and the azepinodiindolones.
Scheme 7: Proposed mechanism for the formation of 22. The order of protonation and allylation is undetermined....
Scheme 8: Proposed mechanism for the formation of 23 from intermediate 29.
Scheme 9: Proposed key branch points and mechanistic sinks in the base-catalysed cascade allylation reactions...
Scheme 10: Reaction of the spiro heterocycle 12 with Grubbs' II catalyst, and X-ray crystal structure of the n...
Beilstein J. Org. Chem. 2012, 8, 1265–1270, doi:10.3762/bjoc.8.142
Figure 1: Binaphthyl-anchored tripeptide derivatives 1.
Scheme 1: Synthesis of compounds 2a–g. Reagents and conditions: (i) 2a–b,d–g, BnBr, acetone or THF, K2CO3, re...