Synthesis of maradolipid

J Org Chem. 2011 Aug 19;76(16):6866-70. doi: 10.1021/jo200979n. Epub 2011 Jul 21.

Abstract

The first synthesis of maradolipid, a unique dissymmetrically 6,6'-di-O-acylated trehalose glycolipid isolated from C. elegans, is accomplished in five steps starting from trehalose in 45% overall yield. The short synthesis relies on dissymmetrization of trehalose core via regioselective acylation of a 2,3,4,2',3',4'-hexa-O-TMS trehalose 6,6'-diol derivative as a key step.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acylation
  • Animals
  • Caenorhabditis elegans / chemistry
  • Glycolipids / chemical synthesis*
  • Glycolipids / chemistry
  • Glycolipids / isolation & purification
  • Molecular Sequence Data
  • Molecular Structure
  • Trehalose / analogs & derivatives
  • Trehalose / chemical synthesis*
  • Trehalose / chemistry

Substances

  • Glycolipids
  • maradolipid
  • Trehalose