Total Synthesis of Lucilactaene, a Cell Cycle Inhibitor Active in p53-inactive Cells

J Am Chem Soc. 2005 Nov 23;127(46):16038-9. doi: 10.1021/ja056217g.

Abstract

Hetero-bis-metalated 1,3-butadiene is employed in the lynchpin coupling of synthetic fragments of the side chain of the antitumor agent, lucilactaene. Sequential Stille and Suzuki-Miyaura couplings interpolate this unique boron/tin diene into the pentaene chain. The total synthesis of lucilactaene was accomplished efficiently, in just eight linear steps.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Cell Cycle / drug effects*
  • Cells / chemistry
  • Cells / metabolism*
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Furans / pharmacology*
  • Molecular Structure
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry
  • Pyrroles / pharmacology*
  • Tumor Suppressor Protein p53 / deficiency*

Substances

  • Furans
  • Pyrroles
  • Tumor Suppressor Protein p53
  • lucilactaene