Asymmetric Total Synthesis of Rumphellclovane E

Org Lett. 2021 Jan 15;23(2):290-295. doi: 10.1021/acs.orglett.0c03748. Epub 2020 Dec 24.

Abstract

The first asymmetric total synthesis of rumphellclovane E, a clovane-type sesquiterpenoid, has been accomplished in eight steps from commercially available (R)-carvone. Key elements of the synthesis include Rh-catalyzed cyclopropanation, iron-catalyzed intramolecular reductive aldol reaction, and SmI2-mediated chemo- and diastereoselective reduction of the cyclopentanone.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry
  • Catalysis
  • Cyclohexane Monoterpenes / chemical synthesis*
  • Cyclohexane Monoterpenes / chemistry
  • Cyclopentanes
  • Molecular Structure
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / chemistry
  • Stereoisomerism

Substances

  • Aldehydes
  • Cyclohexane Monoterpenes
  • Cyclopentanes
  • Sesquiterpenes
  • cyclopentanone
  • carvone
  • 3-hydroxybutanal