Synthetic studies on d-biotin, part 9. An improved asymmetric synthetic route to d-biotin via Hoffmann-Roche lactone-thiolactone approach

Chem Pharm Bull (Tokyo). 2005 Jul;53(7):743-6. doi: 10.1248/cpb.53.743.

Abstract

An efficient and highly stereoselective total synthesis of d-biotin has been achieved starting from cis-1,3-dibenzyl-2-imidazolidone-4,5-dicarboxylic acid (2) with an overall yield of 33%. Polymer-supported oxazaborolidine-catalyzed asymmetric reduction of meso-cyclic imide 4 constitutes the key synthetic step in introducing stereogenic centers into the d-biotin molecule.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biotin / chemical synthesis*
  • Lactones / chemistry*
  • Magnetic Resonance Spectroscopy
  • Spectrometry, Mass, Electrospray Ionization
  • Sulfhydryl Compounds / chemistry*

Substances

  • Lactones
  • Sulfhydryl Compounds
  • Biotin