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Chemoenzymatic total synthesis of hyperiones A and B

Organic and Biomolecular Chemistry, ISSN: 1477-0520, Vol: 11, Issue: 8, Page: 1376-1382
2013
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Article Description

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 cycloisomerization 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. © 2013 The Royal Society of Chemistry.

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