Jatrophane diterpenes

Preparation of the western fragment of pl-3

Christoph Lentsch, Rita Fürst, Johann Mulzer, Uwe Rinner

Research output: Contribution to journalArticle

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

Fingerprint

Diterpenes
fragments
Biological Products
preparation
synthesis
Cyclopentanes
Oxidation
oxidation
Enantiomers
enantiomers
symmetry
products
installing
bromides
routes
Substrates
jatrophane

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

Cite this

Jatrophane diterpenes : Preparation of the western fragment of pl-3. / Lentsch, Christoph; Fürst, Rita; Mulzer, Johann; Rinner, Uwe.

In: European Journal of Organic Chemistry, Vol. 2014, No. 5, 02.2014, p. 919-923.

Research output: Contribution to journalArticle

Lentsch, Christoph ; Fürst, Rita ; Mulzer, Johann ; Rinner, Uwe. / Jatrophane diterpenes : Preparation of the western fragment of pl-3. In: European Journal of Organic Chemistry. 2014 ; Vol. 2014, No. 5. pp. 919-923.
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