Efficient convergent synthesis of 1alpha,25-dihydroxyvitamin D3 and its analogues by Suzuki-Miyaura coupling.
[reaction: see text] 1alpha,25-Dihydroxyvitamin D(3) was synthesized by the Suzuki-Miyaura coupling of the A-ring intermediate 1, which was efficiently prepared from readily available 1,7-enyne 2, with the corresponding boronate compound of the C,D-ring portion. The method was applied to prepare des-C,D analogues of 1alpha,25-dihydroxyvitamin D(3).
Hanazawa
Takeshi
T
Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama, Kanagawa 226-8501, Japan.
Koyama
Akiko
A
Wada
Takeshi
T
Morishige
Eiko
E
Okamoto
Sentaro
S
Sato
Fumie
F
D000480:Alkynes / Q000737:chemistry; D001880:Boranes; D002117:Calcitriol / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D003500:Cyclization; D004811:Epichlorohydrin / Q000737:chemistry; D018020:Lithium Compounds
D000480:Alkynes; D001880:Boranes; D018020:Lithium Compounds; D004811:Epichlorohydrin; C021274:boron trifluoride; D002117:Calcitriol