Gram-scale synthesis of the A'B'-subunit of angelmicin B

Org Lett. 2011 Dec 16;13(24):6436-9. doi: 10.1021/ol202728v. Epub 2011 Nov 15.

Abstract

A gram-scale enantiospecific synthesis of the A'B'-subunit of angelmicin B is reported. The synthesis involves a Lewis acid catalyzed contrasteric Diels-Alder reaction and a tandem silyl zincate 1,6-addition/enolate oxidation sequence.

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

  • Actinobacteria / chemistry
  • Anthraquinones / chemical synthesis*
  • Anthraquinones / chemistry
  • Catalysis
  • Lewis Acids / chemistry
  • Molecular Structure
  • Organosilicon Compounds / chemistry
  • Oxidation-Reduction
  • Stereoisomerism

Substances

  • Anthraquinones
  • Lewis Acids
  • Organosilicon Compounds
  • angelmicin B