- Economical Process for Preparation of the 19-nor A Ring of Paricalcitol from (-)-Shikimic Acid
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An economical and efficient means of preparing the 19-nor A ring, a key precursor of the vitamin D receptor (VDR) activator Paricalcitol, is here described. This process begins with commercially available (-)-shikimic acid and was easily scaled up to kilo
- Zhou, Shengfeng,Zhu, Runyu,Hu, Jingwen,Zhang, Lixiong,Lu, Qian,Yu, Xinhong
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p. 1887 - 1891
(2019/08/26)
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- Preparation method of paricalcitol intermediate
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The invention discloses a preparation method of a paricalcitol intermediate, which includes the following steps: (1) shikimic acid is esterified; (2) hydroxyl groups at sites 3 and 5 are selectively protected; (3) hydroxyl group at site 4 is protected by
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- A new metabolite of Paricalcitol: stereoselective synthesis of (22Z)-isomer of 1α,25-dihydroxy-19-norvitamin D2
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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–Hor
- Samala, Ramakrishna,Sharma, Somesh,Basu, Manas K.,Mukkanti,Porstmann, Frank
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p. 1309 - 1312
(2018/03/26)
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- 1-DEOXY ANALOGS OF VITAMIN D-RELATED COMPOUNDS
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This present disclosure is directed to novel prodrugs of activated vitamin D3 compounds. The prodrugs can be designed to have one or more beneficial properties, such as selective inhibition of the enzyme CYP24, low calcemic activity, and anti-proliferativ
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- HYBRID MOLECULES HAVING MIXED VITAMIN D RECEPTOR AGONISM AND HISTONE DEACETYLASE INHIBITORY PROPERTIES
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Hybrid molecules comprising a vitamin D receptor agonist moiety and an HDAC inhibitor moiety are described herein The HDAC inhibitor moiety can be modelled after an HDAC inhibitor selected from the group consisting of tπchostatm A, sodium butyrate, valpro
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Page/Page column 23; 44
(2008/06/13)
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- Novel versatile approach to an enantiopure 19-nor, des-C,D vitamin D3 derivative
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A short and efficient de novo route to the des-C,D vitamin D3 derivative 3 (Ro 65-2299), a potential antipsoriatic, has been developed. This route features an assembly strategy so far unexplored in vitamin D chemistry involving a modified Julia olefination of the A-ring ketone 30 and the 2-benzothiazolyl sulfone 60. Construction of the A-ring building block was accomplished by an efficient three-step route starting from the meso trans-1,3,5-cyclohexane triol (26), which was desymmetrized by a highly selective enzymatic mono-hydrolysis of the corresponding triacetate 27 followed by oxidation of the alcohol 29 to give the homochiral diacetoxy ketone 30 (ee=99.5%) in 83% overall yield. Furthermore, we found efficient and practical syntheses of the 5-acetoxy-2-cyclohexenone (31) and its enantiomer 32, both new building blocks useful for natural product synthesis.
- Hilpert, Hans,Wirz, Beat
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p. 681 - 694
(2007/10/03)
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- Efficient and practical synthesis of the A-ring precursor of 19-nor-1alpha,25-dihydroxyvitamin D(3) and its (13)C- or (2)H-labeled derivative.
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[reaction: see text] The A-ring precursor of 19-nor-1alpha,25-dihydroxyvitamin D(3) (1) and its (13)C- or (2)H-labeled derivative were efficiently synthesized from readily available, optically active 5-(tert-butyldimethylsilyloxy)-2-cyclohexenone (2) thro
- Hanazawa,Inamori,Masuda,Okamoto,Sato
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p. 2205 - 2207
(2007/10/03)
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- Asymmetric synthesis of a key ring a synthon for 1α-hydroxy-19-nor vitamin D
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A diasteroselective carbonyl ene reaction on a substrate obtained from a regioselective propiolate ene reaction is described for the synthesis of 19- nor A-ring synthon 3.
- Courtney, Lawrence F.,Lange, Meinolf,Uskokovic, Milan R.,Wovkulich, Peter M.
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p. 3363 - 3366
(2007/10/03)
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- "Symmetry" in the synthesis of the A-ring of a vitamin D hybrid analogue with significant transactivation activity: A combinatorial sequence of regioselective propiolate-ene, catalytic enantioselective epoxidation and carbonyl-ene cyclization reactions
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The combination of the regioselective propiolate-ene reaction, catalytic enantioselective epoxidation and catalytic enantioselective carbonyl-ene cyclization completes the synthesis of the A ring of the hybrid 19-nor-22-oxa D3 analogue (1), which shows the significant activity in transactivation.
- Mikami, Koichi,Osawa, Ayako,Isaka, Akira,Sawa, Eiji,Shimizu, Masaki,Terada, Masahiro,Kubodera, Noboru,Nakagawa, Kimie,Tsugawa, Naoko,Okano, Toshio
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p. 3359 - 3362
(2007/10/03)
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- Novel synthesis of 19-nor-vitamin D compounds
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1α,25-Dihydroxy-19-nor-vitamin D3 was prepared efficiently in a convergent synthesis starting with (-)-quinic acid and a ketone of the Windaus-Grundmann type.
- Perlman, Kato L.,Swenson, Rolf E.,Paaren, Herbert E.,Schnoes, Heinrich K.,DeLuca, Hector F.
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p. 7663 - 7666
(2007/10/02)
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