Stereoselective synthesis of C24-hydroxylated vitamin D3 analogs: A practical and expeditius route to calcipotriol

Rumbo, Antonio; Pérez-García, Xenxo; Mouriño, Antonio

doi:10.1016/j.jsbmb.2010.03.074

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Historical Context and Overall Retrosynthetic Plan1

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2022

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“…As such, this powerful method allows for the direct A-ring and triene formation in a single reaction step; however, obtaining the acyclic enyne 18 with high enantiopurity has proved to be a challenge ( 9 ). Finally, Mouriño and coworkers initially developed the reduction/isomerization approach to access the requisite triene system found in the VitD scaffold (Path V) ( 25 , 28 – 31 ).…”

Section: Historical Context and Overall Retrosynthetic Planmentioning

confidence: 99%

Convergent total synthesis of (+)-calcipotriol: A scalable, modular approach to vitamin D analogs

Rodriguez

Kanda

et al. 2022

Proc. Natl. Acad. Sci. U.S.A.

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Significance Vitamin D (VitD), a group of secosteroids, has proved to be an essential molecule in supporting overall human health. Structurally, modification at C20 has led to the discovery of novel analogs with a wide range of biological targets. Among them, calcipotriol (Daivonex; LEO Pharma) has been a proven clinical drug for the treatment of psoriasis, an autoimmune skin disease. This work relates to an improved process for the preparation of intermediates useful for the preparation of a range of VitD derivatives, including calcipotriol, and to processes for preparation of calcipotriol. Strategic bond disconnections enable de novo syntheses of both A- and CD-rings not wedded to semisynthesis.

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