Catalytic synthesis of enantiopure mixed diacylglycerols – synthesis of a major M. tuberculosis phospholipid and platelet activating factor

Org Biomol Chem. 2013 Sep 25;11(40):6919-28. doi: 10.1039/c3ob41483c.

Abstract

An efficient catalytic one-pot synthesis of TBDMS-protected diacylglycerols has been developed, starting from enantiopure glycidol. Subsequent migration-free deprotection leads to stereo- and regiochemically pure diacylglycerols. This novel strategy has been applied to the synthesis of a major Mycobacterium tuberculosis phospholipid, its desmethyl analogue, and platelet activating factor.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cobalt / chemistry*
  • Diglycerides / chemical synthesis
  • Diglycerides / chemistry*
  • Molecular Conformation
  • Mycobacterium tuberculosis / chemistry*
  • Organometallic Compounds / chemistry*
  • Phospholipids / chemical synthesis*
  • Phospholipids / chemistry
  • Platelet Activating Factor / chemical synthesis*
  • Platelet Activating Factor / chemistry
  • Stereoisomerism

Substances

  • Diglycerides
  • Organometallic Compounds
  • Phospholipids
  • Platelet Activating Factor
  • Cobalt