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Issue 8, 2013
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Chemoenzymatic total synthesis of hyperiones A and B

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Abstract

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.

Graphical abstract: Chemoenzymatic total synthesis of hyperiones A and B

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Publication details

The article was received on 24 Oct 2012, accepted on 21 Dec 2012 and first published on 02 Jan 2013


Article type: Paper
DOI: 10.1039/C2OB27073K
Org. Biomol. Chem., 2013,11, 1376-1382

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    Chemoenzymatic total synthesis of hyperiones A and B

    C. Manzuna Sapu and J. Deska, Org. Biomol. Chem., 2013, 11, 1376
    DOI: 10.1039/C2OB27073K

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