title: Synthesis of oligosubstituted bullvalones: shapeshifting molecules under basic conditions.
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.
authors.affiliation: Department of Chemistry and Biochemistry, University of California at Santa Barbara, Santa Barbara, CA 93106-9510, USA.
authors.forename: Alex R
authors.initials: AR
authors.lastname: Lippert
authors.forename: Juthanat
authors.initials: J
authors.lastname: Kaeobamrung
authors.forename: Jeffrey W
authors.initials: JW
authors.lastname: Bode