Asymmetric Total Synthesis of Propindilactone G

J Am Chem Soc. 2015 Aug 19;137(32):10120-3. doi: 10.1021/jacs.5b06480. Epub 2015 Aug 10.

Abstract

A concise total synthesis of (+)-propindilactone G, a nortriterpenoid isolated from the stems of Schisandra propinqua var. propinqua, has been achieved for the first time. The key steps of the synthesis include an asymmetric Diels-Alder reaction, a Pauson-Khand reaction, a Pd-catalyzed reductive hydrogenolysis reaction, and an oxidative heterocoupling reaction. These reactions enabled the synthesis of (+)-propindilactone G in only 20 steps. As a consequence of our synthetic studies, the structure of (+)-propindilactone G has been revised.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Chemistry Techniques, Synthetic
  • Cycloaddition Reaction
  • Oxidation-Reduction
  • Palladium / chemistry
  • Schisandra / chemistry
  • Triterpenes / chemical synthesis*
  • Triterpenes / chemistry

Substances

  • Triterpenes
  • propindilactone G
  • Palladium