Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 11, Issue 8, Pages 1376-1382Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2ob27073k
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- Fonds der Chemischen Industrie
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The first asymmetric total synthesis of hyperiones A and B, two norlignans from Hypericum chinense, has been accomplished following a chemoenzymatic approach. Key features of this synthesis include the lipase-catalyzed enantioselective desymmetrization of a prochiral allenic diol and a silver-mediated cyclo-isomerization of the resulting axially chiral product to furnish the furan core structure. Two alternative pathways, a ruthenium-catalyzed redox isomerization on the one side and a platinum-catalyzed hydrogenation on the other, are described to finally obtain the desired norlignans.
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