Total synthesis of (-)-SNF4435 C and (+)-SNF4435 D

Org Lett. 2005 Sep 29;7(20):4475-7. doi: 10.1021/ol051790q.

Abstract

[reaction: see text] A convergent, biomimetic total synthesis of the immunosuppressant polyketides SNF4435 C and D is described. The synthetic pathway features a stereo- and regioselective [3,3]-sigmatropic rearrangement as well as a high-yielding Stille coupling/8pi-6pi electrocyclization cascade.

Publication types

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

MeSH terms

  • Crystallography, X-Ray
  • Models, Molecular
  • Molecular Structure
  • Nitrites / chemistry
  • Nitro Compounds / chemical synthesis*
  • Nitro Compounds / chemistry
  • Pyrones / chemical synthesis*
  • Pyrones / chemistry
  • Stereoisomerism

Substances

  • Nitrites
  • Nitro Compounds
  • Pyrones
  • SNF 4435C
  • SNF 4435D