The first synthesis and biological testing of the enantiomer of 1α,25-dihydroxyvitamin D3

被引：13

作者：

Achmatowicz, B

Gorobets, E

Marczak, S

Przezdziecka, A

Steinmeyer, A

Wicha, J

Zügel, U

机构：

[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw 42, Poland

[2] Schering AG, Preclin Drug Res, D-13342 Berlin, Germany

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 15期

关键词：

enantioselective synthesis; Mukaiyama-Michael reaction; Mitsunobu reaction; vitamin D;

D O I：

10.1016/S0040-4039(01)00317-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 1 alpha ,25-dihydroxyvitamin D-3 enantiomer was synthesized and examined in biological tests. The ring A precursor was prepared from vitamin D-2 employing the Mitsunobu reaction for inversion of the configuration at C-3 and SeO2 hydroxylation at C-l. The CD rings-side chain portion was synthesized from an optically active hexanoic acid derivative using diastereoselective tandem Mukaiyama-Michael addition and vinylsulfone reduction as the key steps. The ring A and CD rings building blocks were combined using the Julia alkenylation reaction. 1 alpha ,25-Dihydroxyvitamin D-3 enantiomer shows no significant affinity to the vitamin D receptor. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：2891 / 2895

页数：5

共 42 条

[1] CHIRALITY IN BIOACTIVE AGENTS AND ITS PITFALLS [J].