Recent Developments for Introducing a Hexafluoroisopropanol Unit into the Vitamin D Side Chain

Publication date: Available online 14 July 2017
Source:The Journal of Steroid Biochemistry and Molecular Biology
Author(s): Fumihiro Kawagoe, Toru Sugiyama, Motonari Uesugi, Atsushi Kittaka
Among numerous studies on synthetic approaches to and the biological activities of vitamin D analogues, we herein focused on falecalcitriol, an analogue of calcitriol (1α,25-dihydroxyvitamin D3), in which a 26,26,26,27,27,27-hexafluoroisopropanol unit has been introduced into the side chain. Falecalcitriol was designed to escape from the metabolism of CYP24A1 and has been used as a drug to treat secondary hypoparathyroidism since 2001. Its metabolite, the 23-hydroxy form, retains biological activity and resistants to further metabolism. Recent developments in synthetic methodologies for introducing the hexafluoroisopropanol unit into the vitamin D CD-ring side chain were described herein.

Graphical abstract

http://ift.tt/2vnHqWS