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

页码：1190 / 1195

页数：6

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