Quorumolides A-C, Three Cembranoids from Euphorbia antiquorum

J Org Chem. 2018 Jan 19;83(2):1041-1045. doi: 10.1021/acs.joc.7b02684. Epub 2018 Jan 8.

Abstract

Three highly modified cembranoids, quorumolides A-C (1-3), were isolated from Euphorbia antiquorum. Compound 1 is the first example of a cembranoid embedding an α,β-unsaturated-γ-lactone and a tetrahydro-2H-pyran motif within the 14-membered ring. Biosynthetically, it is particularly noteworthy that the stereochemistries of C-2 and C-12 in the pyran ring of 1-3 were opposite to those of marine-derived rare cembranoids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Euphorbia / chemistry*
  • Models, Molecular
  • Molecular Conformation
  • Stereoisomerism

Substances

  • Diterpenes
  • quorumolide A
  • quorumolide B
  • quorumolide C