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Beilstein J. Org. Chem. 2013, 9, 2821–2833, doi:10.3762/bjoc.9.317
Graphical Abstract
Figure 1: Unique structural features of (−)-isosteviol.
Figure 2: Triphenylene ketal based on (−)-isosteviol.
Figure 3: Structural features of triptycene derivatives.
Scheme 1: Functionalization of triphenylene ketal 2a.
Figure 4: Hexaammoniumtriptycene hexachloride 4 and 15-oxo-derivatives 5a–c of (–)-isosteviol.
Scheme 2: Quinoxalines based on diketone 5b.
Scheme 3: Condensation of 5b with hexaammoniumtriptycene hexachloride.
Figure 5: Molecular modelling structures (Spartan ’08 V1.0.0) of (a) all-syn-8 and (b) anti,anti,syn-8.
Scheme 4: Synthesis of nitrobenzylic ester derivatives 10 and 11, starting from (−)-isosteviol 1.
Scheme 5: Condensation of the nitrobenzyl esters 10 and 11 with hexaammoniumtriptycene hexachloride 4.
Scheme 6: Hydrogenolysis to tricarboxylic acid all-syn-16.
Scheme 7: Alkylation of all-syn-16 renders terminal alkene all-syn-17.
Figure 6: (a) Top view on the molecular structure of all-syn-17 with the terminal alkene fragments labelled i...
Scheme 8: Alkylation of (−)-isosteviol diketone 9 with 5-bromo-1-pentene.
Scheme 9: Direct synthesis of alkylated triptycene 17 by condensation of 18 with hexaammoniumtriptycene hexac...
Scheme 10: Olefin metathesis of all-syn-17.
Figure 7: Extracts of the 13C NMR spectra of starting material and product.
Figure 8: Molecular modelling structure (MacroModel 9.3.5) of collapsed 19, (a) top view; (b) side view.
Figure 9: Screening of aromatic analytes with affinity materials 3, 7, 8, 17 and 19.
Figure 10: Primary data of anti,anti,syn-8 and a [3 + 2] cage compound (increasing pseudocumene concentrations...
Figure 11: Screening of protic analytes with affinity materials 3, 8, 14 and 15.