Bioinspired total synthesis of (−)-gymnothelignan L

Peng Chen; Liang Huo; Huilin Li; Lin Liu; Ziyun Yuan; Hao Zhang; Shangbiao Feng; Xingang Xie; Xiaolei Wang; Xuegong She

doi:10.1039/C8QO00026C

Bioinspired total synthesis of (−)-gymnothelignan L†

Peng Chen,^a Liang Huo,^a Huilin Li,^a Lin Liu,^a Ziyun Yuan,^a Hao Zhang,^a Shangbiao Feng,^a Xingang Xie,

^a Xiaolei Wang^a and Xuegong She

*^ab

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* Corresponding authors

^a State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou, China
E-mail: shexg@lzu.edu.cn

^b Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin, China

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.

Organic Chemistry Frontiers

Bioinspired total synthesis of (−)-gymnothelignan L†

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