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Issue 15, 2007
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Bidirectional racemic synthesis of the biologically active quinonecardinalin 3

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Abstract

Readily available 2,2′,6,6′-tetramethoxy-1,1′-biphenyl was transformed in 14 synthetic steps into the natural product cardinalin 3 using a bidirectional approach. One of the key steps was the formation of the cis-1,3-dimethylnaphtho[2,3-c]pyran ring. (±)-1,1′-[6,6′-Diallyl-5,5′-bis(benzyloxy)-1,1′,3,3′-tetramethoxy-2,2′-binaphthalene-7,7′-diyl]diethanol was treated with O2 in the presence of CuCl2 and catalytic PdCl2 to afford 5,5′-bis(benzyloxy)-7,7′,9,9′-tetramethoxy-1,1′,3,3′-tetramethyl-1H,1′H-8,8′-bibenzo[g]isochromene. Hydrogenation of this compound afforded 7,7′,9,9′-tetramethoxy-cis-1,3-cis-1′,3′-tetramethyl-3,3′,4,4′-tetrahydro-1H,1′H-8,8′-bibenzo[g]isochromene-5,5′-diol in quantitative yield, which was converted in 3 steps to cardinalin 3.

Graphical abstract: Bidirectional racemic synthesis of the biologically active quinonecardinalin 3

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Article information


Submitted
11 May 2007
Accepted
04 Jun 2007
First published
26 Jun 2007

Org. Biomol. Chem., 2007,5, 2433-2440
Article type
Paper

Bidirectional racemic synthesis of the biologically active quinonecardinalin 3

S. Govender, E. M. Mmutlane, W. A. L. van Otterlo and C. B. de Koning, Org. Biomol. Chem., 2007, 5, 2433
DOI: 10.1039/B707187F

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