Asymmetric synthesis and anti-protozoal activity of the 8,4'-oxyneolignans virolin, surinamensin and analogues.

Eur J Med Chem 2013 Feb 16;60:240-8. Epub 2012 Dec 16.

School of Chemical Sciences, University of Auckland, 23 Symonds St, Auckland, New Zealand.

The asymmetric synthesis of 8,4'-oxyneolignans (-)-virolin, (-)-surinamensin and a number of analogues has been achieved. A divergent synthesis was used, with all compounds being elaborated from a single chiral aldehyde derived from ethyl lactate. In the 15 compounds that were tested, the level of substitution on the A-ring was found to directly influence the activity against Leishmania donovani whilst the activity against Plasmodium falciparum was influenced by numerous substitution and stereochemical factors.

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http://dx.doi.org/10.1016/j.ejmech.2012.12.013DOI Listing
February 2013
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