Aggreganoids A-F, Carbon-Bridged Sesquiterpenoid Dimers and Trimers from Lindera aggregata

Org Lett. 2019 Jul 19;21(14):5753-5756. doi: 10.1021/acs.orglett.9b02166. Epub 2019 Jul 5.

Abstract

Six oligomeric sesquiterpenoids, aggreganoids A-F (1-6), were isolated from Lindera aggregata. Aggreganoid A (1) and B (2) are two unprecedented methine- or methylene-bridged sesquiterpenoid trimers possessing a unique C46 skeleton. Aggreganoids C-F (3-6) are the first examples of carbon-bridged disesquiterpenoids with a C33 or C31 skeleton in the plant kingdom. Their structures and absolute configurations were elucidated by using spectroscopic methods and electronic circular dichroism calculations. A plausible biosynthetic pathway of these compounds was also proposed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbon / chemistry*
  • Dimerization*
  • Lindera / chemistry*
  • Models, Molecular
  • Molecular Conformation
  • Polymerization*
  • Sesquiterpenes / chemistry*

Substances

  • Sesquiterpenes
  • Carbon