Total synthesis of (±)-sorocenol B employing nanoparticle catalysis

Org Lett. 2012 May 18;14(10):2516-9. doi: 10.1021/ol300800r. Epub 2012 May 3.

Abstract

The total synthesis of (±)-sorocenol B has been accomplished featuring key steps including silver nanoparticle (AgNP)-catalyzed Diels-Alder cycloaddition and late-stage Pd(II)-catalyzed oxidative cyclization. The synthetic natural product exhibited low micromolar cytotoxic activity against a number of human cancer cell lines.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Catalysis
  • Cyclization
  • Cycloaddition Reaction
  • Heterocyclic Compounds, 4 or More Rings / chemistry
  • Humans
  • Metal Nanoparticles / chemistry*
  • Molecular Structure
  • Moraceae / chemistry
  • Oxidation-Reduction
  • Silver / chemistry*
  • Stereoisomerism

Substances

  • Biological Products
  • Heterocyclic Compounds, 4 or More Rings
  • sorocenol B
  • Silver