Total synthesis of biologically active 20S-hydroxyvitamin D3

Academic Article

Abstract

  • A total synthetic strategy of 20S-hydroxyVitamin D3 [20S-(OH)D3] involving modified synthesis of key intermediates 7 and 12, Grignard reaction to stereoselectively generate 20S-OH and Wittig-Horner coupling to establish D3 framework, was completed in 16 steps with an overall yield of 0.4%. The synthetic 20S-(OH)D3 activated Vitamin D receptor (VDR) and initiated the expression of downstream genes. In addition, 20S-(OH)D3 showed similar inhibitory potency as calcitriol [1,25(OH)2D3] on proliferation of melanoma cells.
  • Published In

  • Steroids  Journal
  • Digital Object Identifier (doi)

    Author List

  • Wang Q; Lin Z; Kim TK; Slominski AT; Miller DD; Li W
  • Start Page

  • 153
  • End Page

  • 162
  • Volume

  • 104