Assignment of absolute configuration to SCH 351448 via total synthesis

Org Lett. 2008 Jul 17;10(14):3101-4. doi: 10.1021/ol8011474. Epub 2008 Jun 11.

Abstract

The synthesis and absolute configuration of SCH 351448, an interesting ionophoric natural product, are reported herein. Mukaiyama aldol-Prins and segment-coupling Prins reactions were employed to construct the constituent tetrahydropyrans of SCH 351448. Efforts to assemble the C2-symmetric core of the natural product by a templated olefin metathesis strategy are described; however, a stepwise fragment assembly was ultimately utilized to complete the target molecule.

Publication types

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

MeSH terms

  • Alkenes / chemistry*
  • Biological Products / chemical synthesis*
  • Cyclization
  • Lactones / chemical synthesis*
  • Lactones / chemistry
  • Micromonospora / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • Alkenes
  • Biological Products
  • Lactones
  • SCH 351448