Synthesis of the Bis-Spiroacetal C25-C40 Moiety of the Antimitotic Agent Spirastrellolide B Using a Bis-Dithiane deprotection/spiroacetalisation Sequence

Chem Commun (Camb). 2010 Jun 14;46(22):3967-9. doi: 10.1039/c0cc00056f. Epub 2010 May 5.

Abstract

Use of a bis-dithiane deprotection-tandem bis-spiroacetalisation sequence was key to the successful synthesis of the [5,6,6]-bis-spiroacetal of the antimitotic agent spirastrellolide B, achieved in a highly convergent fashion involving successive dithiane alkylations.

MeSH terms

  • Alkylation
  • Antimitotic Agents / chemical synthesis*
  • Antimitotic Agents / chemistry
  • Macrolides / chemical synthesis*
  • Macrolides / chemistry
  • Protein Phosphatase 2 / antagonists & inhibitors
  • Protein Phosphatase 2 / metabolism
  • Quinolizines / chemistry*
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry
  • Sulfur Compounds / chemistry*

Substances

  • Antimitotic Agents
  • Macrolides
  • Quinolizines
  • Spiro Compounds
  • Sulfur Compounds
  • dithiane
  • spirastrellolide B
  • Protein Phosphatase 2