Synthesis of 1α,25-dihydroxyvitamin D3 analogues with α-hydroxyalkyl substituents at C12

被引：5

作者：

Carballa, Diego M. ^{[1
,2
]}

Zacconi, Flavia ^{[1
,2
]}

Kulesza, Urszula ^{[1
,2
,3
]}

Mourino, Antonio ^{[1
,2
]}

Torneiro, Mercedes ^{[1
,2
]}

机构：

[1] Univ Santiago de Compostela, Dept Quim Organ, CSIC, Santiago De Compostela 15782, Spain

[2] Univ Santiago de Compostela, Unidad Asociada, CSIC, Santiago De Compostela 15782, Spain

[3] Univ Warsaw, Dept Chem, PL-02093 Warsaw, Poland

来源：

JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY | 2013年 / 136卷

关键词：

1; alpha; 25-Dihydroxyvitamin D-3; Vitamin D-3 analogues; Suzuki coupling; Alkenyl boronic esters; Johnson-Claisen rearrangement; VITAMIN-D-RECEPTOR; MECHANISM;

D O I：

10.1016/j.jsbmb.2012.10.010

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Convergent syntheses of three new analogues of 1 alpha,25-dihydroxyvitamin D-3 with alpha-hydroxyalkyl substituents at C12 (4a-c) are described. The A-ring and triene system of each analogue were assembled by a tandem Pd-catalysed intramolecular cyclization and Suzuki-Miyaura coupling process. The stereoselective introduction of substituents at C12 was achieved by Johnson-Claisen rearrangement on allylic alcohol 15 as the key step. This article is part of a Special Issue entitled 'Vitamin D Workshop'. (c) 2012 Elsevier Ltd. All rights reserved.

引用

页码：34 / 38

页数：5

共 21 条

[1]

[Anonymous], LANDSCOPE

[2]

Beckman MJ, 1998, PROGR MED CHEM, V35, P1, DOI 10.1016/S0079-6468(08)70033-X

[3] STRUCTURE-FUNCTION-RELATIONSHIPS IN THE VITAMIN-D ENDOCRINE SYSTEM [J].