Towards the total synthesis of Pl-3

Preparation of the eastern fragment through a diastereoselective SmI2-mediated reformatsky reaction

Rita Fürst, Christoph Lentsch, Uwe Rinner

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

The jatrophane diterpene Pl-3, isolated in 2003 from Euphorbia platyphyllos, is a structurally complex natural product with highly promising biological properties that include pronounced antiproliferative activity and the inhibition of the efflux-pump activity of multidrug resistance p-glycoprotein. Herein, the synthesis of the eastern fragment of Pl-3 is outlined. The target compound is synthesized in nine synthetic operations in good overall yield, starting from readily available D-ribose. The key step in the preparation of the eastern part of Pl-3 is a diastereoselective SmI2-mediated Reformatsky reaction. The proposed route is highly flexible and could also be applied to the synthesis of structurally related jatrophane diterpenes.

Original languageEnglish
Pages (from-to)2293-2297
Number of pages5
JournalEuropean Journal of Organic Chemistry
Issue number12
DOIs
Publication statusPublished - Apr 2013

Fingerprint

Diterpenes
fragments
efflux
ribose
preparation
Ribose
synthesis
Biological Products
Glycoproteins
routes
Pumps
pumps
products
jatrophane

Keywords

  • Diastereoselectivity
  • Multidrug resistance
  • Natural products
  • Samarium
  • Terpenoids

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

Cite this

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