Synthesis of antimicrobial natural products targeting FtsZ: (+)-totarol and related totarane diterpenes

Org Lett. 2010 Aug 6;12(15):3324-7. doi: 10.1021/ol100929z.

Abstract

An efficient, convergent synthesis of totarol by a diastereoselective epoxide/alkene/arene bicyclization is described. The reported synthesis enables the preparation of related diterpenes totaradiol and totarolone as well as previously unavailable derivatives that exhibit comparable inhibition of the bacterial cell division protein FtsZ.

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

  • Abietanes
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Bacterial Proteins / antagonists & inhibitors*
  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Biological Products / pharmacology*
  • Cytoskeletal Proteins / antagonists & inhibitors*
  • Diterpenes / chemical synthesis*
  • Diterpenes / chemistry
  • Diterpenes / pharmacology*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Abietanes
  • Anti-Bacterial Agents
  • Bacterial Proteins
  • Biological Products
  • Cytoskeletal Proteins
  • Diterpenes
  • FtsZ protein, Bacteria
  • totaradiol
  • totarolone
  • totarol