A Stereospecific Synthesis of 24(S)-Hydroxyvitamin D2, a Prodrug for 1α,24(S)-Dihydroxyvitamin D2
Organic Process Research & Development2002Vol. 6(3), pp. 246–255
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Lisa D. Coutts, William Geiss, Brian T. Gregg, Mark Helle, Chi-Hsin R. King, Z. I. Itov, Mary E. Mateo, Harold Meckler, Mark W. Zettler, Joyce C. Knutson
Abstract
This contribution describes the first stereospecific synthesis of 24(S)-hydroxyvitamin D2 (1), a metabolite of vitamin D2. This metabolite acts as a prodrug for 1α,24(S)-dihydroxyvitamin D2 (2), which is under development for treatment of various diseases characterized by cellular hyperproliferation. The key step of the synthesis involves the Wittig−Horner olefination of (S)-2,3-dimethyl-2-triethysilyloxybutyraldehyde (17) and a vitamin D2 phosphine oxide derivative (22). The synthesis of the requisite aldehyde started with the commercially available l-(+)-valine and was completed in seven steps. The vitamin D2 phosphine oxide derivative was synthesized in seven steps starting from vitamin D2.
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