Total Synthesis of (-)-Bacchopetiolone via an Asymmetric Hydroxylative Phenol Dearomatization/[4+2]-Dimerization Cascade Promoted by a Novel Salen-Type Chiral Iodane

Org Lett. 2016 Mar 4;18(5):1120-3. doi: 10.1021/acs.orglett.6b00224. Epub 2016 Feb 23.

Abstract

The first total and biomimetic synthesis of the natural bis(sesquiterpene) (-)-bacchopetiolone (revised structure) was completed through a highly diastereoselective hydroxylative phenol dearomatization/[4+2]-dimerization cascade conversion of (+)-curcuphenol using a novel C2-symmetrical chiral Salen-type bis(λ(5)-iodane).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetophenones / chemistry
  • Catalysis
  • Cyclization
  • Molecular Structure
  • Phenols / chemistry
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / chemistry
  • Stereoisomerism

Substances

  • Acetophenones
  • Phenols
  • Sesquiterpenes
  • bacchopetiolone
  • curcuphenol