A novel and practical route to A-ring enyne synthon for 1 alpha,25-dihydroxyvitamin D3 analogs: synthesis of A-ring diastereomers of 1 alpha,25-dihydroxyvitamin D2 and 3-methyl-1,25-dihydroxyvitamin D3

Bioorg Med Chem Lett. 1998 Jan 20;8(2):151-6. doi: 10.1016/s0960-894x(97)10204-9.

Abstract

A novel and practical route to the A-ring enyne synthon (2), which can be versatile for a variety of A-ring analogs of 1 alpha,25-dihydroxyvitamin D3 (1), was developed. This novel method led to an improved synthesis of the A-ring diastereomers of 1, the compounds 13-15, and synthesis of the new analogs, 2-methyl-1,25-dihydroxyvitamin D3 (4) with its all possible diastereomers. The biological evaluation of the 2-methyl analogs showed the alpha alpha beta-isomer to be more potent than 1.

MeSH terms

  • Calcitriol / analogs & derivatives*
  • Calcitriol / chemical synthesis
  • Calcitriol / pharmacology
  • Stereoisomerism
  • Structure-Activity Relationship
  • Vitamin D / analogs & derivatives*
  • Vitamin D / chemical synthesis
  • Vitamin D / chemistry
  • Vitamin D / pharmacology

Substances

  • 2-methyl-1,25-dihydroxyvitamin D3
  • Vitamin D
  • Calcitriol