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Synthesis of Oligosubstituted Bullvalones: Shapeshifting Molecules Under Basic Conditions

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NIAID Data Ecosystem2026-03-06 收录
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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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2016-05-12
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