19: Chance and Design: An Historical Perspective of the Chemistry of Oral Contraceptives (1974)

Authors

  • Arthur John Birch Research School of Chemistry, Australian National University

Abstract

The 19th Liversidge Research Lecture, delivered before the Royal Society of New South Wales, 15th August, 1974. Reproduced by permission of the Royal Society of New South Wales from J. Proc. Roy. Soc. N.S.W., 1974, 107, 100-113.

"The requirement of total synthesis of sex and cortical hormones is discussed in the historical context of evolution of ideas and techniques leading to biologically active analogues. In particular, the desire to make 18- and 19-norsteroids led to development of the technique of metal-ammonia reductions and eventually to the 19-norsteroid hormones used as oral contraceptives. This history is considered against a background of the role of chance and design in scientific research in general and pharmaceutical research in particular."

Author Biography

  • Arthur John Birch, Research School of Chemistry, Australian National University

     

    In 1974, Arthur John Birch was the Foundation Dean of Organic Chemistry at ANU. He is most well-known for the Birch Reduction – the alkali-metal/ammonia reduction of aromatic ring systems. Later in his career, Birch became involved with science policy and administration. He was, among others, at one point the President of the Royal Australian Chemical Institute, Chair of an independent inquiry into the CSIRO, and OECD Examiner on Science and Technology Policy in Demark.

     

    For additional biographical information, photographic permissions, references and a list of honours, awards and publications, please see pages 2–4 of the transcript.

References

Ananchenko, S.N., and Torgov, N., 1959. Dokl. Akad.Nauk. SSSR, 127, 553. cf. 1963, Tet. Lett., 1553.

Anner, G., and Miescher, K., 1948. Helv., 31, 2173.

Bachmann, W.E., Cole, W., and Wilds, A.L., 1939. J. Amer. Chem. Soc., 61, 974.

Barber G.W., and Ehrenstein, M., 1957. Annalen, 603, 89.

Birch, A.J., 1944. J. Chem. Soc., 430.

Birch, A.J., 1950a. Ann. Rep. Chem. Soc., p. 210.

Birch, A.J., 1950b. J. Chem. Soc., 2325.

Birch, A.J., 1951b. Yearbook of the Royal Society, p. 196.

Birch A.J., 1951a. Chem. & Ind., 616.

Birch A.J., and Mukherji, S.M., 1949b. Nature, 163, 766.

Birch, A.J., and Mukherji, S.M., 1949a. J. Chem. Soc., 2531. cf. Birch, A.J., 1950. J. Chem. Soc., 367.

Birch, A.J., and Robinson, R., 1943. J. Chem. Soc., 501.

Birch, A.J., and Robinson, R., 1944a. J. Chem. Soc., 501.

Birch, A.J., and Robinson, R., 1944b. J. Chem. Soc., 503.

Birch, A.J., and Smith, H., 1956. J. Chem. Soc., 4909. cf. 1951. J. Chem. Soc., 1882.

Birch, A.J., and Subba Rao, G.S.R., 1970. Aust. J. Chem., 23, 547.

Birch, A.J., and Subba Rao, G., 1972. Advances in Organic Chemistry. (Ed. E. C. Taylor.) John Wiley & Sons, 8, 1-65.

Birch, A.J., Brown, J.M., and Subba Rao, G.S.R., 1964. J. Chem. Soc., 3309.

Birch, A.J.,Jaeger, R.H., and Robinson, R., 1945. J. Chem. Soc., 582.

Birch, A.J., Quartey, J.A.K., and Smith, H., 1952. J. Chem. Soc., 1768.

Campbell, K.N., and Campbell, B.K., 1942. Chem. Rev., 31, 77.

Campbell, N.R., Dodds, E.C., and Lawson, W., 1938. Nature, 142, 1121. cf. Dodds, E.C., and Lawson, W., 1937. Nature, 139, 627, 1068.

Cardwell, H.M.E., Cornforth, J.W., Duff, S.R., Holtermann, H., and Robinson, R., 1951. Chem. and Ind., 389.

Colton, F.B., 1955. U.S. Patent 2,725,389.

Colton F.B., Nysted, L.N., Riegel, B., and Raymond, A.L., 1957. J. Amer. Chem. Soc., 79, 1123.

Cornforth, J.W., Cornforth, R.H., and Robinson, R., 1942. J. Chem. Soc., 689.

Dirscherl, L., Kraus, J., and Voss, H.E., 1936. Z. Physiol. Chem., 241, 1.

Djerassi, C., 1966. Science, 151, 1055.

Djerassi, C., Miramontes, L., Rosenkranz, G., and Sondheimer, F., 1954. J.Amer. Chem. Soc., 76, 4092.

Djerassi, C., Miramontes, L., Rosenkranz, G., and Sondheimer, F., 1954. A.C.S. Meeting, April 1952. Div. Med. Chem. Abs., p. 18J.

Dodds E.C., Golberg, L. Lawson, W., and Robinson, R., 1939. Proc. Roy. Soc., B., 127, 140.

Douglas, G.H., Graves, J.M.H., Hartley, D., Hughes, G.A., McLoughlin, B.J., Siddall, J., and Smith, H., 1963. J. Chem. Soc., 5072.

Dumanskii, A.V., and Zvyerava, A.V., 1916. J. Russ. Phys. Chem. Soc., 48, 994. (Chem. Abs. 11, 787).

Ehrenstein, M., 1944. J. Org. Chem., 9, 435.

Fieser, L.F., and Fieser M., 1959a. Steroids, Reinhold, New York. 1959b. Ibid, p. 586.

Kazanskii, B.A., and Glushnev, N. F., 1938. J. Gen. Chem. USSR., 8, 642.

Kharasch, M.S., and Tawney, P.O., 1941. J. Amer. Chem. Soc., 63, 2308.

Koebner, A., and Robinson, R., 1938. J. Chem. Soc., 1994.

Miramontes, L., Rosenkranz, G., and Djerassi, C., 1951. J. Amer. Chem. Soc., 73, 3540. cf.

Djerassi, C., Miramontes, L., and Rosenkranz, G., 1953. J. Amer. Chem. Soc., 75, 4440.

Narashima Rao, P., and Axelrod, L. A., 1965. J. Chem. Soc., 1356.

Smith, H., Hughes, G.A., Douglas, G. H., Wendt, G. R., Buzby, G. C., Edgren, R. A., Fisher, J., Foell, T., Gadsby, B., Hartley D., Herbst, D., Jansen, A.B.A., Ledig, K., McLoughlin, B.J., McMenamin, J., Pattison, T.W., Phillips, P.C., Rees, R., Siddall, J., Siuda, J., Smith, L.L., Tokolics, J., and Watson, D.H.P., 1964. J. Chem. Soc., 4472.

Snyder, H.R., and Werber, F. X., 1950. J. Amer. Chem. Soc., 72, 2965.

Stavely, H.E., 1939. J. Amer. Chem. Soc., 61, 79.

Stork, G., Khastgir, H. N., and Solo, A. J., 1958. J. Amer. Chem. Soc., 80, 6457. cf. Johns W. F., 1958. J. Amer. Chem. Soc., 80, 6456, and Anliker, R., Muller, M., Perelman, M., Wohlfahrt, J., and Jeusser, H., 1959. HeIv., 42, 1071.

Wilds, A.L., and Nelson, N. A., 1953. J. Amer. Chem. Soc., 75, 5360, 5366.

Wooster, C.B., and Godfrey, K. L., 1937. J. Amer. Chem. Soc., 59, 596. cf. Wooster, C.B., 1939. U.S. Patent, 2,182,242. (Chem. Abs., 34, 1993).

Arthur John Birch portrait.

Downloads