Novel synthetic approach to 19-nor-1alpha,25-dihydroxyvitamin D(3) and its derivatives by Suzuki-Miyaura coupling in solution and on solid support.
19-nor-1alpha,25-Dihydroxyvitamin D(3) was synthesized by the Suzuki-Miyaura coupling of the A-ring intermediate 3, which was efficiently prepared from readily available 5-(tert-butyldimethylsilyl)oxycyclohex-2-enone (5), with the boronate compound of the C,D-ring portion. The method could be applied to a solid-phase synthesis to prepare the des-C,D derivatives of 19-nor-1alpha,25-dihydroxyvitamin D(3). [reaction: see text]
Hanazawa
T
T
Department of Biomolecular Engineering, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama, Kanagawa 226-8501, Japan.
Wada
T
T
Masuda
T
T
Okamoto
S
S
Sato
F
F
D002117:Calcitriol / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D012996:Solutions
D012996:Solutions; C083610:1,25-dihydroxy-19-norvitamin D3; D002117:Calcitriol