Efficient and practical synthesis of the A-ring precursor of 19-nor-1alpha,25-dihydroxyvitamin D(3) and its (13)C- or (2)H-labeled derivative.
[reaction: see text] The A-ring precursor of 19-nor-1alpha,25-dihydroxyvitamin D(3) (1) and its (13)C- or (2)H-labeled derivative were efficiently synthesized from readily available, optically active 5-(tert-butyldimethylsilyloxy)-2-cyclohexenone (2) through a five-step reaction in 68% overall yield.
Hanazawa
T
T
Department of Biomolecular Engineering, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama, Kanagawa 226-8501, Japan.
Inamori
H
H
Masuda
T
T
Okamoto
S
S
Sato
F
F
D002117:Calcitriol / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D002247:Carbon Isotopes / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D003512:Cyclohexanones / Q000737:chemistry*; D003903:Deuterium / Q000737:chemistry; D007553:Isotope Labeling; D015394:Molecular Structure; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
C432704:5-(tert-butyldimethylsilyloxy)-2-cyclohexenone; D002247:Carbon Isotopes; D003512:Cyclohexanones; D012821:Silanes; D003903:Deuterium; D002117:Calcitriol