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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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Article information


Submitted
24 Oct 2012
Accepted
21 Dec 2012
First published
02 Jan 2013

Org. Biomol. Chem., 2013,11, 1376-1382
Article type
Paper

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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