Summary
Starting from 6-methoxynaphthaldehyde-2, 2-carboxy-7-methoxy-1, 2, 3, 4-tetrahydrophenanthrone-4 was prepared. Sodium borohydride reduction of the keto-acid followed by chromic acid oxidation yielded the lactone of 2-carboxy-4-hydroxy-7-methoxy-1, 2, 3, 4-tetrahydrophenanthrone. Alkylation of the lactone of 2-carboxy-4-hydroxy-6-methoxytetralone was not promising.
Similar content being viewed by others
References
Simpson, S. A. and Tait, J. F.Recent Progress in Hormone Research, 1955,11, 208.
Banerjee, D. K. and Bagavant, G.Proc. Ind. Acad. Sci., 1959,50 A, 282.
Tard, C., Lapin, H. and Horeau, A.Compt. Rend., 1958,246, 3644.
Robinson, R. and Slater, S. N.J. Chem. Soc., 1941, 376.
Woodward, R. B. and Eastman, R. H.J. Amer. Chem. Soc., 1944,66, 674.
Eglinton, G., Nevenezel, J. C., Scott, A. I. and Newman, M. S. Ibid., 1956,78, 2331.
Papa, D., Schwenk, E. and Whitman, B.J. Org. Chem., 1942,7, 587.
—— and Ginsberg, H. F. Ibid., 1944,9, 1.
Johnson, W. S...Organic Reactions, Vol. II, John Wiley and Sons, Inc., New York, 1944, p. 116.
Bachmann, W. E. and Chemerda, J. M.J. Amer. Chem. Soc., 1948,70, 1472.
Uehlinger, H. P., Ch. Tamm and Reichstein, T.Hel. Chim. Acta, 1957,40, 2234.
Poos, G. I., Arth, G. E., Bayler, R. E. and Sarett, L. H.J. Amer. Chem. Soc., 1953,75, 425.
Stork, G., Loweenthal, H. J. E. and Mukharji, P. C. Ibid., 1956,78, 501.
Bredt, J., Thoubet, H. and Schmitz, H.Ann., 1924,437, 4.
Fawcett, F. S...Chem. Revs., 1950,47, 249.
Prelog, V. ..J. Chem. Soc., 1950, 425.
Gilman, H., Beel, J. A., Brannen, C. G., Bullock, M. W., Dunn, G. E. and Miller, L. S.J. Amer. Chem. Soc., 1949,71, 1499.
Wilds, A. L. and Shunk, C. H. Ibid., 1943,65, 471.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Banerjee, D.K., Bagavant, G. Synthesis of the lactone of 2-carboxy-4-hydroxy-7-methoxy-1, 2, 3, 4-tetrahydrophenanthrone. Proc. Indian Acad. Sci. 53, 113–122 (1961). https://doi.org/10.1007/BF03045798
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF03045798