Chemoenzymatic total synthesis of hyperiones A and B

Jan Deska; Chicco Manzuna Sapu

doi:10.1039/C2OB27073K

Chemoenzymatic total synthesis of hyperiones A and B

Jan Deska, Chicco Manzuna Sapu

Not published at Aalto University

Research output: Contribution to journal › Article › Scientific › peer-review

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.

Original language	English
Pages (from-to)	1376-1382
Number of pages	7
Journal	ORGANIC AND BIOMOLECULAR CHEMISTRY
Volume	11
DOIs	https://doi.org/10.1039/C2OB27073K
Publication status	Published - 21 Dec 2012
MoE publication type	A1 Journal article-refereed

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Deska, J., & Sapu, C. M. (2012). Chemoenzymatic total synthesis of hyperiones A and B. ORGANIC AND BIOMOLECULAR CHEMISTRY, 11, 1376-1382. https://doi.org/10.1039/C2OB27073K

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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.",

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AB - 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.

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