A stereospecific synthesis of 24 (S)-hydroxyvitamin D2, a prodrug for 1α, 24 (S)-dihydroxyvitamin D2

LD Coutts, WB Geiss, BT Gregg, MA Helle…

Index: Coutts, Lisa D.; Geiss, William B.; Gregg, Brian T.; Helle, Mark A.; King, Chi-Hsin R.; Itov, Zinovy; Mateo, Mary E.; Meckler, Harold; Zettler, Mark W.; Knutson, Joyce C. Organic Process Research and Development, 2002 ,  vol. 6,  # 3  p. 246 - 255

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Citation Number: 16

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 ...