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Novel synthetic approach to 19-nor-1alpha,25-dihydroxyvitamin D(3) and its derivatives by Suzuki-Miyaura coupling in
1Department of Biomolecular Engineering, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama, Kanagawa 226-8501, Japan.
Organic Letters
|November 27, 2001
Abstract:
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]