
Tetrahedron Letters p. 2891 - 2895 (2001)
Update date:2022-09-26
Topics:
Achmatowicz, Barbara
Gorobets, Evgueni
Marczak, Stanislaw
Przezdziecka, Agnieszka
Steinmeyer, Andreas
Wicha, Jerzy
Zügel, Ulrich
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.
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