Linderalides A-D, Disesquiterpenoid-Geranylbenzofuranone Conjugates from Lindera aggregata

J Org Chem. 2019 Jun 21;84(12):8242-8247. doi: 10.1021/acs.joc.9b00522. Epub 2019 Jun 10.

Abstract

Four disesquiterpenoid-geranylbenzofuranone conjugates, linderalides A-D (1-4), were isolated from Lindera aggregata. Compounds 1-3 represent the first examples of disesquiterpenoid-geranylbenzofuranone hybrids directly linked by two C-C bonds. Linderalide D (4) bears an unprecedented carbon skeleton featuring an unusual linearly 6/6/5/6/6 pentacyclic ring system fused by a sesquiterpenoid unit and a geranylbenzofuranone moiety. Their structures and absolute configurations were elucidated by extensive spectroscopic data and electronic circular dichroism analysis. Their biosynthetic pathways were also proposed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzofurans / chemistry*
  • Lindera / chemistry*
  • Plant Roots / chemistry
  • Sesquiterpenes / chemistry*
  • Stereoisomerism

Substances

  • Benzofurans
  • Sesquiterpenes
  • benzofuran