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Bioinspired total synthesis of (−)-gymnothelignan L

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Abstract

The first asymmetric total synthesis of gymnothelignan L has been accomplished in 14 steps with 11.2% overall yield. The synthetic approach features an anti Evans aldol reaction, a diastereoselective methylation, a Suzuki–Miyaura coupling and a bioinspired desymmetric transannular Friedel–Crafts reaction. Notably, the synthesis further demonstrated the biogenetic pathway that dibenzocyclooctene-type lignans are generated from eupomatilone-type lignans.

Graphical abstract: Bioinspired total synthesis of (−)-gymnothelignan L

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Publication details

The article was received on 10 Jan 2018, accepted on 21 Jan 2018 and first published on 22 Jan 2018


Article type: Research Article
DOI: 10.1039/C8QO00026C
Citation: Org. Chem. Front., 2018, Advance Article
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    Bioinspired total synthesis of (−)-gymnothelignan L

    P. Chen, L. Huo, H. Li, L. Liu, Z. Yuan, H. Zhang, S. Feng, X. Xie, X. Wang and X. She, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C8QO00026C

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