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Synfacts 2007(9): 0906-0906  
DOI: 10.1055/s-2007-968833
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (-)-Ovalicin

Contributor(s): Philip Kocienski, Zofia Komsta
K. Tiefenbacher, V. B. Arion, J. Mulzer*
Universität Wien, Austria
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Publication History

Publication Date:
23 August 2007 (online)

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Significance

(-)-Ovalicin exhibits potent anti­angiogenic and antimicrosporidiosis activity. The diastereoselective Diels-Alder reaction of Trost’s diene A (B. Trost, L. Chupak, T. Lübbers J. Org. Chem. 1997, 62, 736) with 2-bromopropenal established adjacent 2° and 3° stereogenic centers in cycloadduct C from which the remaining stereogenic centers were constructed.