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Synthesis of Oligosubstituted Bullvalones: Shapeshifting Molecules Under Basic Conditions

2006; American Chemical Society; Volume: 128; Issue: 46 Linguagem: Inglês

10.1021/ja063900+

1943-2984

Alex R. Lippert, Juthanat Kaeobamrung, Jeffrey W. Bode,

Asymmetric Synthesis and Catalysis

Oligosubstituted bullvalones were synthesized in eight steps from 2,6-cycloheptadienone via a unique Lewis acid catalyzed intramolecular cyclopropanation of a stabilized sulfur ylide, leading directly to the tetracyclic cage structure. Upon exposure to base, the substituted bullvalones tautomerized to a hydroxybullvalene, which underwent dynamic interconversion into numerous, structurally distinct bullvalones. This system represents a "self-contained" dynamic combinatorial library in which the dynamic nature can be modulated by external reagents.