Isolation and biomimetic synthesis of (±)-guajadial B, a novel meroterpenoid from Psidium guajava

Org Lett. 2012 Dec 7;14(23):5936-9. doi: 10.1021/ol302849v. Epub 2012 Nov 19.

Abstract

(±)-Guajadial B (1), an unusual humulene-based meroterpenoid, was isolated as a racemate from the leaves of Psidium guajava, collected from Vietnam. The structure of this novel secondary metabolite was established on the basis of extensive analysis of NMR spectra and confirmed by biomimetic synthesis in a domino three-component coupling reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Molecular Structure
  • Monocyclic Sesquiterpenes
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Leaves / chemistry
  • Psidium / chemistry*
  • Sesquiterpenes / chemistry
  • Stereoisomerism
  • Terpenes / chemical synthesis*
  • Terpenes / chemistry
  • Vietnam

Substances

  • Monocyclic Sesquiterpenes
  • Sesquiterpenes
  • Terpenes
  • guajadial B
  • humulene