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

Nat Commun. 2019 Apr 23;10(1):1892. doi: 10.1038/s41467-019-09858-8.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chemistry Techniques, Synthetic*
  • China
  • Cycloaddition Reaction
  • Dimerization
  • Magnoliopsida / chemistry*
  • Magnoliopsida / metabolism
  • Molecular Structure
  • Plant Extracts / chemistry
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / isolation & purification

Substances

  • Plant Extracts
  • Sesquiterpenes