Jatrophane diterpenes: Preparation of the western fragment of pl-3

Christoph Lentsch, Rita Fürst, Johann Mulzer, Uwe Rinner

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8 Citations (Scopus)

Abstract

Jatrophane diterpenes are structurally intriguing natural products with promising biological properties. Herein, the synthesis of the western fragment of the Euphorbiaceae constituent Pl-3 starting from (1R,5S)-bicyclo[3.2.0]hept- 2-en-6-one is described. Key steps in the sequence include a Baeyer-Villiger oxidation, an iodolactonization reaction, and the installation of the northern side chain through the addition of a lithiated vinyl bromide. The overall efficiency of the route is increased by taking advantage of latent symmetry. The synthesis of the western fragment of Pl-3 is developed by taking advantage of the latent symmetry in an intermediate; both enantiomers are thus converted into the desired substrate. Key steps of the synthesis include a Baeyer-Villiger oxidation, an iodolactonization reaction, and the addition of a vinyllithium species to the completed cyclopentane moiety of the natural product.

Original languageEnglish
Pages (from-to)919-923
Number of pages5
JournalEuropean Journal of Organic Chemistry
Volume2014
Issue number5
DOIs
Publication statusPublished - Feb 2014

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Keywords

  • Lithium
  • Medicinal chemistry
  • Natural products
  • Oxidation
  • Terpenoids
  • Total synthesis

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

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