Total synthesis of borrelidin

J Org Chem. 2007 Apr 13;72(8):2744-56. doi: 10.1021/jo062089i. Epub 2007 Mar 14.


The total synthesis of borrelidin has been achieved. The best feature of our synthetic route is macrocyclization at C11-C12 for the construction of an 18-membered ring after esterification between two segments. A detailed examination of the macrocyclization led us to the samarium(II) iodide-mediated intramolecular Reformatsky-type reaction as the most efficient synthetic approach. The two key segments were synthesized through regioselective methylation, directed hydrogenation, stereoselective Reformatsky-type reaction, and MgBr2.Et2O-mediated chelation-controlled allylation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Fatty Alcohols / chemical synthesis
  • Fatty Alcohols / chemistry
  • Molecular Structure
  • Stereoisomerism


  • Fatty Alcohols
  • borrelidin