An efficient synthesis of 1α,25-dihydroxy-20-epi-vitamin D3

被引:7
作者
Fraga, R. [1 ]
Lopez-Perez, B. [1 ]
Sokolowska, K. [1 ]
Guini, A. [1 ]
Regueira, T. [1 ]
Diaz, S. [1 ]
Mourino, A. [1 ]
Maestro, M. A. [2 ]
机构
[1] Univ Santiago de Compostela, Dept Quim Organ, E-15782 Santiago De Compostela, Spain
[2] Univ A Coruna, Dept Quim Fundamental, E-15071 La Coruna, Spain
关键词
Vitamin D analogues synthesis; 1; alpha; 25-Dihydroxy-20-epi-vitamin D-3; MC1288; Palladium(0)-catalyzed coupling; VITAMIN-D; ANALOGS; REGULATORS;
D O I
10.1016/j.jsbmb.2013.01.010
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
The synthesis of 1 alpha,25-dihydroxy-20-epi-vitamin D-3 (1) by Pd(0)-catalyzed coupling between the boronate ester (2) and the enol triflate (3) is described. This article is part of a Special Issue entitled 'Vitamin D Workshop'. (c) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:14 / 16
页数:3
相关论文
共 19 条
[1]   20-EPI-VITAMIN-D3 ANALOGS - A NOVEL CLASS OF POTENT REGULATORS OF CELL-GROWTH AND IMMUNE-RESPONSES [J].
BINDERUP, L ;
LATINI, S ;
BINDERUP, E ;
BRETTING, C ;
CALVERLEY, M ;
HANSEN, K .
BIOCHEMICAL PHARMACOLOGY, 1991, 42 (08) :1569-1575
[2]  
BROWN AJ, 1994, SEMIN NEPHROL, V14, P156
[3]  
Calverley M., 1991, PCT Int. Appl., Patent No. [WO9100271A1, 9100271]
[4]  
DeLuca H., 1996, Patent No. [US 5552392 A, 5552392]
[5]  
DILWORTH FJ, 1994, BIOCHEM PHARMACOL, V47, P987
[6]   Vitamin D heterocyclic analogues.: Part 1:: A stereoselective route to CD systems with pyrazole rings in their side chains [J].
Fall, Y ;
Barreiro, C ;
Fernández, C ;
Mouriño, A .
TETRAHEDRON LETTERS, 2002, 43 (08) :1433-1436
[7]   Efficient synthesis and biological evaluation of all A-ring diastereomers of 1α,25-dihydroxyvitamin D3 and its 20-epimer [J].
Fujishima, T ;
Konno, K ;
Nakagawa, K ;
Kurobe, M ;
Okano, T ;
Takayama, H .
BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (01) :123-134
[8]   NOVEL REAGENT SYSTEM FOR CONVERTING A HYDROXY-GROUP INTO AN IODO-GROUP IN CARBOHYDRATES WITH INVERSION OF CONFIGURATION [J].
GAREGG, PJ ;
SAMUELSSON, B .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (22) :978-980
[9]  
Gongoi P., 2010, CHEM-EUR J, V16, P1432
[10]   Effect of 20-epi-1α,25-dihydroxyvitamin D3 on the proliferation of human neuroblastoma:: role of cell cycle regulators and the Myc-Id2 pathway [J].
Gumireddy, K ;
Ikegaki, N ;
Phillips, PC ;
Sutton, LN ;
Reddy, CD .
BIOCHEMICAL PHARMACOLOGY, 2003, 65 (12) :1943-1955