Synthesis of Diastereomers of 1,3-cis-25-Dihydroxy-19-norvitamin D3

Chem Pharm Bull (Tokyo). 2016;64(8):1190-5. doi: 10.1248/cpb.c16-00311.

Abstract

1β,3β,25-Dihydroxy-19-norvitamin D3 (4a) and 1α,3α,25-dihydroxy-19-norvitamin D3 (4b) were synthesized by employing a new A-ring synthon, (1R,3S)-3-((tert-butyldimethylsilyl)oxy)-5-oxocyclohexyl benzoate (19), which was derived from D-(-)-quinic acid in 12 steps. The A-ring was coupled with the circular dichroism (CD) ring by means of Julia-Kocienski olefination to construct the diene unit. The structures of the products were confirmed by (1)H-NMR and nuclear Overhauser effect (NOE) experiments.

MeSH terms

  • Calcitriol / analogs & derivatives*
  • Calcitriol / chemical synthesis
  • Calcitriol / chemistry
  • Molecular Structure
  • Quinic Acid / chemistry*
  • Stereoisomerism

Substances

  • Quinic Acid
  • 1,25-dihydroxy-19-norvitamin D3
  • Calcitriol