Lathyranoic acid A: first secolathyrane diterpenoid in nature from Euphorbia lathyris

Org Lett. 2005 Mar 31;7(7):1379-82. doi: 10.1021/ol050206a.

Abstract

[structures: see text] Lathyranoic acid A (1), the first secolathyrane diterpenoid with an unprecedented skeleton, and a new diterpenoid Euphorbia factor L11 (2) were isolated from the seeds of Euphorbia lathyris. Their structures were elucidated by spectroscopic analysis and chemical methods. A biogenetic route involving an enzymatic Baeyer-Villiger oxidation as the key step was postulated for the transformation of 2 to 1 and mimicked by an unusual chemical Baeyer-Villiger oxidation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Euphorbia / chemistry*
  • Medicine, Chinese Traditional*
  • Oxidation-Reduction
  • Seeds / chemistry

Substances

  • Diterpenes
  • lathyranoic acid A