Abstract
IN 1935, Windaus, Lettré and Schenck1 described the preparation from cholesterol (I) of 7-dehydrocholesterol (III), which on irradiation gave a highly antirachitic product (vitamin D3), later2 shown to be identical with the naturally occurring vitamin D isolated from tunny liver oil. The original route to provitamin D3, giving an overall conversion from cholesterol of about 4 per cent, has since been employed for the synthesis of several related dehydrosteroids3, but it has not been materially improved, although some useful minor modifications have been described4. Claims5 have been made for alternative and improved methods, but, so far as we are aware, none of these has proved entirely satisfactory.
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References
Windaus, A., Lettré, R., and Schenck, F., Ann., 520, 98 (1935).
Brockmann, H., Z. physiol. Chem., 241, 104 (1936); 245, 96 (1937).
Inter alia Linsert, O., Z. physiol. Chem., 241, 125 (1936). Wunderlich, W., Z. physiol. Chem., 241, 116 (1936). Haslewood, G. A. D., Biochem. J., 33, 454 (1939). Butenandt, A., Hausmann, E., and Paland, J., Ber., 71, 1316 (1938). Ruigh, W. A. L., J. Amer. Chem. Soc., 64, 1900 (1942). Bergmann, W., Lyon, A. M., and McLean, M. J., J. Org. Chem., 9, 290 (1944).
Haslewood, G. A. D., J. Chem. Soc., 224 (1938). Wintersteiner, O., and Ruigh, W. L., J. Amer. Chem. Soc., 64, 1177 (1942).
For example, Milas, N. A., and Heggie, R., J. Amer. Chem. Soc., 60, 984 (1938). Mazza, F. P., and Migliardi, G., Chem. Abstracts, 37, 3762 (1943).
Ziegler, K., et al., Ann., 551, 80 (1942).
See also B.P. 574, 432.
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HENBEST, H., JONES, E., BIDE, A. et al. A New Route to 7-Dehydrocholesterol, Provitamin D3. Nature 158, 169 (1946). https://doi.org/10.1038/158169a0
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DOI: https://doi.org/10.1038/158169a0
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