Industrial synthesis of Maxacalcitol, the antihyperparathyroidism and antipsoriatic vitamin D3 analogue exhibiting low calcemic activity

…, T Mikami, K Tsuzaki, H Suwa, K Harada…

Index: Shimizu, Hitoshi; Shimizu, Kazuki; Kubodera, Noboru; Mikami, Tetsuhiro; Tsuzaki, Kaname; Suwa, Hiroyuki; Harada, Koji; Hiraide, Akira; Shimizu, Motoki; Koyama, Kaichiro; Ichikawa, Yoshihide; Hirasawa, Daisuke; Kito, Yasushi; Kobayashi, Mio; Kigawa, Masaharu; Kato, Masahiro; Kozono, Toshiro; Tanaka, Hideki; Tanabe, Makoto; Iguchi, Masanori; Yoshida, Mitsutaka Organic Process Research and Development, 2005 ,  vol. 9,  # 3  p. 278 - 287

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Citation Number: 19

Abstract

Maxacalcitol, the 22-oxa-derivative of 1α, 25-dihydroxyvitamin D3 and used currently as an antihyperparathyroidism and antipsoriatic drug, has been synthesized in seven chemical steps from 1α-hydroxydehydroepiandrosterone on the basis of our previously developed route. The present synthesis allows the production of the protected form of the penultimate intermediate in 26% overall yield in a kilogram scale reaction employing neither difficult ...