Author/Authors :
Achmatowicz، نويسنده , , Barbara and Gorobets، نويسنده , , Evgueni and Marczak، نويسنده , , Stanis?aw and Przezdziecka، نويسنده , , Agnieszka and Steinmeyer، نويسنده , , Andreas and Wicha، نويسنده , , Jerzy and Zügel، نويسنده , , Ulrich، نويسنده ,
Abstract :
The 1α,25-dihydroxyvitamin D3 enantiomer was synthesized and examined in biological tests. The ring A precursor was prepared from vitamin D2 employing the Mitsunobu reaction for inversion of the configuration at C-3 and SeO2 hydroxylation at C-1. 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. 1α,25-Dihydroxyvitamin D3 enantiomer shows no significant affinity to the vitamin D receptor.
Keywords :
enantioselective synthesis , Mukaiyama–Michael reaction , Mitsunobu reaction , Vitamin D
