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Tetrahedron Letters
Volumn 13, Issue 40, 1972, Pages 4147-4150
The synthesis of 1α,25-dihydroxycholecalciferol -- A metabolically active form of vitamin D3
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EID: 0012663855     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(01)94260-1     Document Type: Article
Times cited : (128)
References (14)
  • 7
    • 84918201628 scopus 로고    scopus 로고
    • Tlc on silica gel G, ethylacetate-cyclohexane 3:1.
  • 8
    • 84918201627 scopus 로고    scopus 로고
    • By analogy with published (ref. 5) and our own results on reduction of 1α,2α-epoxy-3-ketones of the cholesterol series, the 1α,3β-diol should have been obtained as the major product. It appears that this product may have been lost on chromatography because of its significantly greater polarity. Assignment of configuration to epoxide 10 and products 11 and 13 is based on published data (ref. 5), our own model experiments involving preparation and reactions of 1α,2α-epoxycholestan-3-one and 25-desoxy-10, and detailed analysis of the C-19 proton resonances of all derivatives, which in magnitude and direction of chemical shift are in accord with predictions based on published shift increments (e.g. A.I. Cohen and S. Rock, Jr. Steroids 3, 243, 1964)) for ring A substituents (e.g. C-19-H for 7, 67Hz; 10, 58Hz; 11, 52Hz; 12, 65Hz; 13, 55Hz; at 60 mc).
  • 10
    • 84918201626 scopus 로고    scopus 로고
    • 1-3-keto compound and comparison with purified intermediate 9.
  • 13
    • 84918201625 scopus 로고    scopus 로고
    • Intermediates were checked for homogeneity by tlc and/or glc. The elemental composition of most intermediates was determined by accurate mass measurement of the molecular ion at high resolution. For simple derivatives of the main intermediates (e.g. acetates) composition was inferred from the low resolution mass spectrum.
  • 14
    • 84918201624 scopus 로고    scopus 로고
    • This research was supported by grants from the National Institutes of Health, Nos. AM-14881, AM-15512, and GM00236-BCH. We thank Drs. Babcock and Campbell (the Upjohn Company) for generously providing starting material for this synthesis. We also wish to thank Professors Barry Trost and Charles Sih for helpful discussions concerning this synthesis.

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