Synthesis of Diastereomers of 1,3-cis-25-Dihydroxy-19-norvitamin D3

被引：5
|
作者：
Usuda, Kosuke [1 ]
Biswas, Tanima [2 ]
Yamaguchi, Takuya [1 ]
Akagi, Yusuke [1 ]
Yasui, Koji [1 ]
Uesugi, Motonari [3 ,4 ]
Shimizu, Isao [2 ]
Hosokawa, Seijiro [2 ]
Nagasawa, Kazuo [1 ]
机构：
[1] Tokyo Univ Agr & Technol, Grad Sch Technol, 2-14-16 Naka Cho, Koganei, Tokyo 1848588, Japan
[2] Waseda Univ, Fac Sci & Technol, Shinjuku Ku, 3-4-1 Okubo, Tokyo 1698555, Japan
[3] Kyoto Univ, Inst Integrated Cell Material Sci WPI iCeMS, Sakyo Ku, Kyoto 6068115, Japan
[4] Kyoto Univ, Inst Chem Res, Kyoto 6110011, Japan
来源：
CHEMICAL & PHARMACEUTICAL BULLETIN | 2016年 / 64卷 / 08期
关键词：
19-norvitamin D-3; cis-A ring synthon; Julia-Kocienski coupling; VITAMIN-D-RECEPTOR; 1-ALPHA; 25-DIHYDROXY-19-NORVITAMIN D-3; BIOLOGICAL EVALUATION; EFFICIENT SYNTHESIS; ANALOGS; DERIVATIVES; DIFFERENTIATION;
D O I：
10.1248/cpb.c16-00311
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
1 beta,3 beta,25-Dihydroxy-19-norvitamin D-3 (4a) and 1 alpha,3 alpha,25-dihydroxy-19-norvitamin D-3 (4b) were synthesized by employing a new A-ring synthon, (1R,3S)-3-((tert-butyldimethylsilyl)oxy)-5-oxocyclohexyl benzoate (19), which was derived from D-(-)-quinic acid in 12 steps. The A-ring was coupled with the circular dichroism (CD) ring by means of Julia Kocienski olefination to construct the diene unit. The structures of the products were confirmed by H-1-NMR and nuclear Overhauser effect (NOE) experiments.
引用
收藏
页码：1190 / 1195
页数：6
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