Synthesis of a ring-expanded bryostatin analogue

J Am Chem Soc. 2007 Feb 28;129(8):2206-7. doi: 10.1021/ja067305j. Epub 2007 Feb 6.

Abstract

A ring expanded bryostatin analogue was synthesized by utilizing a Ru-catalyzed tandem tetrahydropyran formation, a Pd-catalyzed tandem dihydropyran formation, and a ring-closing metathesis (RCM) as key steps. The analogue possesses potent anti-tumor activity against the NCI-ADR cancer cell line with an IC50 of 123 nM.

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

  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Drug Screening Assays, Antitumor
  • Humans
  • Macrolides / chemical synthesis*
  • Macrolides / chemistry
  • Macrolides / pharmacology
  • Molecular Conformation
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Macrolides