Chemo- and Diastereoselective Hydrosilylation of Amorphadiene toward the Synthesis of Artemisinin

J Org Chem. 2020 Aug 7;85(15):9607-9613. doi: 10.1021/acs.joc.0c00617. Epub 2020 Jul 9.

Abstract

A formal synthesis of artemisinin starting from amorphadiene is described. This new route relies on the development of a catalytic chemo- and diastereoselective hydrosilylation. The practicability of this method is demonstrated by converting amorphadiene to dihydroartemisinic aldehyde using a one-pot hydrosilylation/oxidation sequence, minimizing the number of purifications and maximizing the productivity through a practical one-pot procedure. In addition, this approach can be coupled with a crystallization-induced diastereoselective transformation (CIDT) to enhance the optical purity of the key target intermediate, dihydroartemisinic aldehyde.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Artemisinins*
  • Polycyclic Sesquiterpenes

Substances

  • Artemisinins
  • Polycyclic Sesquiterpenes
  • amorpha-4,11-diene