A new metabolite of Paricalcitol: stereoselective synthesis of (22Z)-isomer of 1α, 25-dihydroxy-19-norvitamin D2. Issue 12 (23rd March 2016)

• Record Type: Journal Article
• Authors: Samala, Ramakrishna; Sharma, Somesh; Basu, Manas K.; Mukkanti, K.; Porstmann, Frank
• Is Part Of: Tetrahedron letters. Volume 57:Issue 12(2016)
• Page Start: 1309
• Page End: 1312
• Publication Date: 2016-03-23
• Subjects: Paricalcitol -- 19-Nor-1, 25-(OH)2-vitamin D2 -- Vitamin D2 (Ergocalciferol) -- d-(−)-Quinic acid -- Julia–Lythgoe's olefination -- Horner–Wadsworth–Emmons reaction; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.01.110
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: Stereoselective synthesis of (22 Z )-isomer of Paricalcitol, an analog of 1, 25-dihydroxyergocalciferol, an active form of vitamin D2 (Ergocalciferol) has been described. The two key critical synthetic steps involved are Julia–Lythgoe's Wittig–Horner coupling of aldehyde functionality of CD-ring system with benzothiazolyl sulfone, and Horner–Wadsworth–Emmons reaction of phosphine oxide with a Windaus–Grundmann's ketone to build a diene motif between the A and CD-ring system of Paricalcitol.