Chemoenzymatic synthesis of trans-tetrahydrofuran cores of annonaceous acetogenins from bromobenzene

Org Lett. 2013 Apr 19;15(8):1982-5. doi: 10.1021/ol400650v. Epub 2013 Mar 29.

Abstract

Two types of trans-THF cores, present in acetogenins, have been synthesized by an intramolecular iodoetherification reaction. The starting alkenol was obtained in a few steps from a chiral cis-diol resulting from microbial oxidation of bromobenzene. The cyclization gave complete stereoselectivity for trans-THF cores with either (S,S) or (R,R) configurations at the THF chiral carbons.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetogenins / chemical synthesis*
  • Acetogenins / chemistry
  • Alcohols / chemistry
  • Annonaceae / chemistry
  • Bromobenzenes / chemistry*
  • Cyclization
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Acetogenins
  • Alcohols
  • Bromobenzenes
  • Furans
  • tetrahydrofuran