C-Aryl glycosides via tandem intramolecular benzyne-furan cycloadditions. Total synthesis of vineomycinone B2 methyl ester

J Am Chem Soc. 2006 Oct 25;128(42):13696-7. doi: 10.1021/ja0652619.

Abstract

A triply convergent total synthesis of vineomycinone B2 methyl ester has been achieved by an approach with a longest linear sequence of 16 steps. The synthesis features the use of silicon tethers as disposable linkers to control the regiochemistry in two tandem Diels-Alder reactions of substituted benzynes and glycosyl furans to provide rapid access to the fully intact anthrarufin core of vineomycinone B2 methyl ester.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anthraquinones / chemical synthesis*
  • Antibiotics, Antineoplastic / chemical synthesis*
  • Benzene Derivatives / chemistry*
  • Cyclization
  • Esters / chemical synthesis*
  • Fucose / analogs & derivatives*
  • Fucose / chemical synthesis
  • Furans / chemistry*
  • Glycosides / chemical synthesis*
  • Methylation
  • Models, Chemical
  • Streptomyces / chemistry*

Substances

  • Anthraquinones
  • Antibiotics, Antineoplastic
  • Benzene Derivatives
  • Esters
  • Furans
  • Glycosides
  • vineomycinone B2 methyl ester
  • Fucose
  • vineomycin B2