Synthesis of 1α,25-Dihydroxyvitamin D Analogues Featuring a S2-symmetric CD-ring Core

Molecules

Garrett Minne¹  Lieve Verlinden²  Annemieke Verstuyf² 

[1] Department of Organic Chemistry, Ghent University, Krijgslaan 281, B-9000 Gent, Belgium;Laboratory of Experimental Medicine and Endocrinology, Catholic University of Leuven, Gasthuisberg, Herestraat 49, B-3000 Leuven, Belgium

关键词: Suzuki coupling;    Sonogashira reaction;    Calcitriol analogues.;   

DOI  :  10.3390/molecules14020894

来源: mdpi

【 摘 要 】

Three analogues of 1α,25-dihydroxyvitamin D₃ (calcitriol), featuring a trans-fused decalin C,D-core with local S₂-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.

【 授权许可】

CC BY   
© 2009 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland.