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Synfacts 2006(3): 0193-0193  
DOI: 10.1055/s-2006-931923
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Interiotherin A

Contributor(s): Philip Kocienski
R. S. Coleman*, S. Reddy Gurrala, S. Mitra, A. Raao
Ohio State University, Columbus, USA
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Publication History

Publication Date:
21 February 2006 (online)

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Significance

Short asymmetric syntheses of dibenzocyclooctadiene lignans Interiotherin A (shown), Angeloylgomisin, Gomisin R and Gomisin O were accomplished by expeditious use of an oxidative biaryl coupling reaction in a very hindered environment. The atropdiastereoselective biaryl coupling (G → H) was accomplished by oxidation of a mixed cuprate intermediate by 1,3-dinitrotoluene according to B. H. Lipshutz, F. Kayser, Z.-P. Liu Angew. Chem. Int. Ed. 1994, 33, 1842-1844 and references therein.