A unified strategy toward total syntheses of lindenane sesquiterpenoid [4 + 2] dimers

Biao Du, Zhengsong Huang, Xiao Wang, Ting Chen, Guo Shen, Shaomin Fu and Bo Liu ()
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Biao Du: Sichuan University
Zhengsong Huang: Sichuan University
Xiao Wang: Sichuan University
Ting Chen: Sichuan University
Guo Shen: Sichuan University
Shaomin Fu: Sichuan University
Bo Liu: Sichuan University

Nature Communications, 2019, vol. 10, issue 1, 1-8

Abstract: Abstract The dimeric lindenane sesquiterpenoids are mainly isolated from the plants of Chloranthaceae family. Structurally, they have a crowded molecular scaffold decorated with more than 11 stereogenic centers. Here we report divergent syntheses of eight dimeric lindenane sesquiterpenoids, shizukaols A, C, D, I, chlorajaponilide C, multistalide B, sarcandrolide J and sarglabolide I. In particular, we present a unified dimerization strategy utilizing a base-mediated thermal [4 + 2] cycloaddition between a common furyl diene, generated in situ, and various types of dienophiles. Accordingly, all the three types of lindenane [4 + 2] dimers with versatile biological activities are accessible, which would stimulate future probing of their pharmaceutical potential.

Date: 2019
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DOI: 10.1038/s41467-019-09858-8

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