Development of a new building block for the synthesis of silicon-based drugs and odorants:: Alternative synthesis of the retinoid agonist disila-bexarotene

被引:28
作者
Buettner, Matthias W. [1 ]
Naetscher, Jennifer B. [1 ]
Burschka, Christian [1 ]
Tacke, Reinhold [1 ]
机构
[1] Univ Wurzburg, Inst Anorgan Chem, D-97074 Wurzburg, Germany
关键词
D O I
10.1021/om700570f
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
With 4,4,5,5-tetramethyl-2-(3,5,5,8,8-pentamethyl-5,8-disila-5,6,7,8-tetrahydro-2-naphthyl)-1,3,2-dioxaborolane (5) a new building block for the synthesis of biologically active 5,8-disila-5,6 7.8-tetrahydronaphthalene derivatives has been made available. The high synthetic potential of 5 has been demonstrated b, v the development of a new synthesis of the retinoid agonist disila-bexarotene (1).
引用
收藏
页码:4835 / 4838
页数:4
相关论文
共 18 条
[1]   STEREOSELECTIVE SYNTHESIS OF ALCOHOLS .30. E-PENTENYLBORONATES AND Z-PENTENYLBORONATES, REAGENTS FOR SIMPLE DIASTEREOSELECTION ON ADDITION TO ALDEHYDES [J].
ANDERSEN, MW ;
HILDEBRANDT, B ;
KOSTER, G ;
HOFFMANN, RW .
CHEMISCHE BERICHTE, 1989, 122 (09) :1777-1782
[2]  
[Anonymous], 2015, Acta Crystallogr., V71, P3
[3]   Silicon analogues of the musk odorant versalide [J].
Buettner, Matthias W. ;
Penka, Martin ;
Doszczak, Leszek ;
Kraft, Philip ;
Tacke, Reinhold .
ORGANOMETALLICS, 2007, 26 (05) :1295-1298
[4]  
BUTTNER MW, 2007, IN PRESS CHEMBIOCHEM
[5]  
Chemler SR, 2001, ANGEW CHEM INT EDIT, V40, P4544, DOI 10.1002/1521-3773(20011217)40:24<4544::AID-ANIE4544>3.0.CO
[6]  
2-N
[7]  
CHEMLER SR, 2001, J ANGEW CHEM, V113, P4767
[8]   Synthesis, crystal structure analysis, and pharmacological characterization of disila-bexarotene, a disila-analogue of the RXR-selective retinoid agonist bexarotene [J].
Daiss, JO ;
Burschka, C ;
Mills, JS ;
Montana, JG ;
Showell, GA ;
Fleming, I ;
Gaudon, C ;
Ivanova, D ;
Gronemeyer, H ;
Tacke, R .
ORGANOMETALLICS, 2005, 24 (13) :3192-3199
[9]   Novel ligand-free, cobalt-catalyzed [2+2+2] cycloadditions: Syntheses of 1,4-disilatetralines and 1,3-disilaindanes [J].
Doszczak, Leszek ;
Fey, Philipp ;
Tacke, Reinhold .
SYNLETT, 2007, (05) :753-756
[10]   Synthesis of fused arylboronic esters via cobalt(0)-mediated cycloaddition of alkynylboronates with α,ω-diynes [J].
Gandon, V ;
Leca, D ;
Aechtner, T ;
Vollhardt, KPC ;
Malacria, M ;
Aubert, C .
ORGANIC LETTERS, 2004, 6 (19) :3405-3407