A new metabolite of Paricalcitol: stereoselective synthesis of (22Z)-isomer of 1α,25-dihydroxy-19-norvitamin D₂

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• 作者：Ramakrishna Samala^a ; Somesh Sharma^a ; ^{somesh.sharma@gvkbio.com" class="auth_mail" title="E-mail the corresponding author} ; Manas K. Basu^a ; K. Mukkanti^a ; Frank Porstmann^b
• 关键词：Paricalcitol ; 19-Nor-1 ; 25-(OH)2-vitamin D2 ; Vitamin D2 (Ergocalciferol) ; d-(&minus ; )-Quinic acid ; Julia&ndash ; Lythgoe&rsquo ; s olefination ; Horner&ndash ; Wadsworth&ndash ; Emmons reaction
• 刊名：Tetrahedron Letters
• 出版年：2016
• 出版时间：23 March 2016
• 年：2016
• 卷：57
• 期：12
• 页码：1309-1312
• 全文大小：733 K

文摘

Stereoselective synthesis of (22Z)-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.