Synthesis of the A-B subunit of angelmicin B

Org Lett. 2005 Nov 24;7(24):5501-4. doi: 10.1021/ol052321r.

Abstract

[reaction: see text] An efficient synthesis of the tricyclic A-B subunit 2 of angelmicin B is described. A formal three-component coupling of aldehydes 4 and 6 with gamma-silylallylborane 7 was employed to assemble the tetrahydrofuranyl core of 2, a strategy highlighted by the stereoselective [3 + 2] annulation of allylsilanes 5a/5b with aldehyde 4. The efficiency of the [3 + 2] annulation was greatly improved by using the allylic benzhydryldimethylsilane 5b compared to the allylic phenyldimethylsilane 5a.

Publication types

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

MeSH terms

  • Aldehydes / chemistry
  • Anthraquinones / chemical synthesis*
  • Anthraquinones / chemistry*
  • Boron Compounds / chemistry
  • Catalysis
  • Molecular Structure
  • Organosilicon Compounds / chemistry
  • Stereoisomerism

Substances

  • Aldehydes
  • Anthraquinones
  • Boron Compounds
  • Organosilicon Compounds
  • angelmicin B