Asymmetric Total Synthesis of Propindilactone G, Part 1: Initial Attempts towards the Synthesis of Schiartanes

Chem Asian J. 2016 May 6;11(9):1406-13. doi: 10.1002/asia.201600129. Epub 2016 Apr 21.

Abstract

Our first-generation synthetic study towards the total synthesis of propindilactone G (1) and its analogues is reported. The key synthetic steps were an intramolecular Pauson-Khand reaction (PKR) and a vinylogous Mukaiyama reaction (VMAR). The stereoselective synthesis of the CDE ring moiety with an all-carbon quaternary center through a PKR was difficult, whilst a VMAR afforded a product with the opposite stereochemistry at the C20 position on the side chain. These results led us to redesign our synthetic strategy for the total synthesis of compound 1.

Keywords: natural products; nortriterpenoids; propindilactone G; synthetic methods; total synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Models, Molecular
  • Molecular Conformation
  • Stereoisomerism
  • Triterpenes / chemical synthesis*
  • Triterpenes / chemistry

Substances

  • Triterpenes
  • propindilactone G
  • schiartane