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Communication

Synthesis of Oligosubstituted Bullvalones: Shapeshifting Molecules Under Basic Conditions

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

Department of Chemistry and Biochemistry, University of California at Santa Barbara, Santa Barbara, California 93106-9510

J. Am. Chem. Soc., 2006, 128 (46), pp 14738–14739

DOI: 10.1021/ja063900+

Publication Date (Web): October 27, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, bode@chem.ucsb.edu

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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Published In Issue November 22, 2006
Received June 4, 2006

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Communication

Synthesis of Oligosubstituted Bullvalones: Shapeshifting Molecules Under Basic Conditions

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

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