Structure and Synthesis of 25-HydroxychoIecaIciferol-26,23-lactone, a Metabolite of Vitamin D

Journal of Organic Chemistry

Volumn 46, Issue 17, 1981, Pages 3422-3428

  Morris, David S ^a   Williams, Dudley H ^a   Norris, Alan F ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

25 HYDROXYCOLECALCIFEROL 23,26 LACTONE; DRUG ANALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; THEORETICAL STUDY; ULTRAVIOLET RADIATION; X RAY ANALYSIS;

EID: 0019501117     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00330a007     Document Type: Article

References (10)

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6. Egert, E.; Cruse, W. B. T.; Kennard, O., paper in preparation.
7. Hollis, B. W.; Ross, B. A.; Lambert, P. S. Biochem. Biophys. Res. Commun. 1980, 95, 520
8. Partridge, J. J.; Shiuey, S.-J.; Chadha, N. K.; Baggiolini, E. G.; Confalone, P. N.; Kuelsha, I.; Wovkulich, P.; Uskokovic, M. R. “Abstracts of the Third IUPAC Symposium on Organic Synthesis”; Madison, WI, June 15-20, 1980; p 74. Partridge, J. J.; Shiuey, S.-J.; Chadka, N. K.; Baggiolini, E. G.; Blount, J. F.; Uskokovic, M. R. J. Am. Chem. Soc. 1981, 103, 1253. See also: Redel, J.; Bazely, N.; Tanaka, Y.; DeLuca, H. F. FEBS Lett. 1980, 113, 345.
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10. A referee has informed us that other workers, in work not currently published, have not been able to establish that (25S)-25,26-dihydroxyvitamin D3 is the precursor of 25-hydroxycholecalciferol-26,23-lactone. Our conclusion that the lactone possesses the 23fi,25S stereochemistry relies on the only published evidence available to us.7 If this evidence is invalidated by subsequent publications, then the possibility that the lactone has the 23S,25R stereochemistry will still exist.