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

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.

SUBMITTER: Du B

PROVIDER: S-EPMC6478710 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature

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

Du Biao B Huang Zhengsong Z Wang Xiao X Chen Ting T Shen Guo G Fu Shaomin S Liu Bo B

Nature communications 20190423 1

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 ...[more]

PMID: 31015442

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