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  • Synthesis of oligosubstituted bullvalones: shapeshifting molecules under basic conditions.

Synthesis of oligosubstituted bullvalones: shapeshifting molecules under basic conditions.

Journal of the American Chemical Society (2006-11-16)
Alex R Lippert, Juthanat Kaeobamrung, Jeffrey W Bode
ABSTRACT

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.

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Sigma-Aldrich
Scandium(III) triflate, 99%