Author:

Keywords:

suzuki coupling, sonogashira reaction, calcitriol analogues, cross-coupling reaction, vitamin-d-receptor, organoboron compounds, biological-activity, organic-chemistry, ligand, d-3, Science & Technology, Life Sciences & Biomedicine, Physical Sciences, Biochemistry & Molecular Biology, Chemistry, Multidisciplinary, Chemistry, Suzuki coupling, Sonogashira reaction, Calcitriol analogues, VITAMIN-D-RECEPTOR, BIOLOGICAL-ACTIVITY, Calcitriol, Molecular Structure, Vitamins, 0304 Medicinal and Biomolecular Chemistry, 0305 Organic Chemistry, 0307 Theoretical and Computational Chemistry, Organic Chemistry, 3404 Medicinal and biomolecular chemistry, 3405 Organic chemistry

Abstract:

Three analogues of 1 alpha,25-dihydroxyvitamin D-3 (calcitriol), featuring a transfused decalin C, D-core with local S-2-symmetry, and possessing identical side-chain and seco-B,A-ring structures, have been synthesized starting from readily available (4aR, 8aS)octahydronaphthalene-1,5-dione(7). The very short sequences involve the simultaneous introduction of the side-chain and seco-B, A-ring fragments via Suzuki and Sonogashira coupling reactions. The analogues are devoid of relevant biological activity.