Synthetic study on telomerase inhibitor, D8646-2-6: synthesis of the key intermediate using Sn(OTf)2 or Sc(OTf)3 mediated aldol-type reaction and Stille coupling

Chem Pharm Bull (Tokyo). 2007 Mar;55(3):495-9. doi: 10.1248/cpb.55.495.

Abstract

The synthesis of the key intermediate (4) in the proposed route to D8646-2-6 is described. The aldol reaction of the carbohydrate-containing pyrone 7 with the aldehyde 6 was accomplished by using LiHMDS and Sc(OTf)3 or Sn(OTf)2. The stepwise dehydration reaction of the aldol adduct 14, followed by Stille coupling with vinyl stannane 5 which contained phosphonate gave the desired 4.

MeSH terms

  • Catalysis
  • Enzyme Inhibitors / chemical synthesis
  • Glycosides / chemical synthesis*
  • Molecular Structure
  • Scandium / chemistry*
  • Telomerase / antagonists & inhibitors*
  • Tin Compounds / chemistry*

Substances

  • D8646-2-6
  • Enzyme Inhibitors
  • Glycosides
  • Tin Compounds
  • Telomerase
  • Scandium