Design and synthesis of a 1α,25-dihydroxyvitamin D3 dimer as a potential chemical inducer of vitamin D receptor dimerization

Pérez Sestelo, J.; Mouriño, A.; Sarandeses, L. A.


Org. Lett. 1999, 1, 1005–1007 (DOI: 10.1021/ol990878z).

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A dimer comprising two 1a,25-dihydroxyvitamin D3 units linked by an alkyl side chain at C-11 was synthesized with a view to the simultaneous binding of two vitamin D receptor (VDR) molecules and the consequent induction of VDR dimerization. The short, convergent synthesis uses a stereoselective cuprate addition to introduce the linking side chain and a key ruthenium olefin metathesis as the dimerization step.