Total synthesis of clavilactone B: a radical cyclization-fragmentation strategy

Org Lett. 2015 Jan 2;17(1):126-9. doi: 10.1021/ol503356m. Epub 2014 Dec 16.

Abstract

A new synthetic route to clavilactone B, a naturally occurring inhibitor of epidermal growth factor receptor (EGFR) tyrosine kinase, is disclosed. The route features a sequential samarium-mediated radical cyclization-fragmentation of an indanone derivative, which provides rapid access to a 10-membered carbocyclic motif fused to an aromatic ring.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Cyclization
  • ErbB Receptors / antagonists & inhibitors*
  • Iodides / chemistry
  • Lactones / chemical synthesis*
  • Lactones / chemistry
  • Molecular Conformation
  • Molecular Structure
  • Samarium / chemistry

Substances

  • Iodides
  • Lactones
  • clavilactone B
  • Samarium
  • ErbB Receptors
  • samarium diiodide