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Synthesis of Functionalized Chiral Carbocyclic Cleft Molecules Complementary to Troeger's Base Derivatives

Kimber, Marc C; Try, Andrew C; Painter, Leoni; Harding, Margaret; Turner, Peter


The synthesis of optically pure functionalized cleft molecules derived from dibenzobicyclo[b,f][3.3.1]nona-5a,6a-diene-6,12-dione is reported. These clefts are reminiscent of Troger's base but contain clefts with different dimensions and additional carbonyl (or alcohol) groups that may be utilized in molecular recognition studies. The 2,8-dimethyl and 2,8-dibromo derivatives were synthesized via an intramolecular Friedel-Crafts acylation and were resolved by chiral HPLC. The 2,8-dinitro...[Show more]

CollectionsANU Research Publications
Date published: 2000
Type: Journal article
Source: Journal of Organic Chemistry
DOI: 10.1021/jo991741p


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