Chapter 1 spouse components in ldl cholesterol of assorted resources (pages 1–26): Louis F. Fieser
Chapter 2 The Chemistry of Lanosterol (pages 27–38): D. H. R. Barton
Chapter three The Ergosterol path to Adrenal Cortical Hormones (pages 39–45): H. B. Henbest and E. R. H. Jones
Chapter four Investigations at the Synthesis of 11?Ketosteroids (pages 46–58): H. Heusser and O. Jeger
Chapter five Partial Synthesis of ?9(11)?Anhydrocorticosterone Acetate (pages 59–64): R. Casanova, A. Ruff and C. W. Shoppee
Chapter 6 Cortisone and 11?Epi?17?Hydroxycorticosterone Diacetate from Sarmentogenin (pages 65–78): A. Lardon and T. Reichstein
Chapter 7 Synthesis of 11?Oxygenated Steroids from Steroidal Sapogenins (pages 79–95): Carl Djerassi and G. Rosenkranz
Chapter eight 11?Oxygenated Steroids from Ergosteryl?D Acetate 22:23?Dibromide (pages 96–103): F. S. Spring, G. T. Newbold, R. C. Anderson, R. Budziarek, F. Johnson, J. A. Mcewan, D. Maclean and R. Stevenson
Chapter nine creation of the 11?Keto functionality within the Steroids (pages 104–109): J. M. Constantin and L. H. Sarett
Chapter 10 The Characterization of Trisubstituted Steroidal Olefines by means of Infra?Red Spectroscopy (pages 110–126): H. Hirschmann
Chapter eleven a few points of the Stereochemistry of C?20 (pages 127–141): W. Klyne
Chapter 12 The Chemical motion of X?Rays on a few Steroids in Aqueous platforms (pages 142–160): Joseph Weiss
Chapter thirteen Biogenesis of Adrenal Cortical Hormones (pages 161–175): Oscar Hechter
Chapter 14 experiences of the Enzymes fascinated with the Synthesis and Degradation of the Hormones of the Adrenal Cortex (pages 176–190): Leo T. Samuels
Chapter 15 The in vitro Synthesis of Adrenal Cortical Steroids (pages 191–209): Ralph I. Dorfman, Mika Hayano, Robert Haynes and Kenneth Savard
Chapter sixteen Species alterations and different elements Influencing Adrenocortical Secretion (pages 210–232): I. E. Bush
Chapter 18 In vivo Metabolism of Adrenosterone (pages 233–239): Ralph I. Dorfman, Kenneth Savard and Shlomo Burstein
Chapter 18 present prestige of Corticosteroid Metabolism in guy (pages 240–260): G. Pincus, E. B. Romanoff and Louise P. Romanoff
Chapter 19 Estimation of person Adrenocortical Hormones in Human Peripheral Blood (pages 261–271): C. J. O. R. Morris and D. C. Williams
Chapter 20 Corticosteroid Metabolism in remoted Perfused Rat Livers (pages 272–289): Oscar Hechter
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Additional resources for Ciba Foundation Symposium - Synthesis and Metabolism of Adrenocortical Steroids (Colloquia on Endocrinology), Volume VII
F. McGhie and his associates at Chelsea Polytechnic, London. Lanosterol, C,,H,,O, has one secondary hydroxyl group and two double bonds. The secondary hydroxyl group is flanked by -CH,- and by -CMe,-. This is shown by the reactions outlined below (Ruzicka, Rey and Muhr, 1944; Ruzicka, Montavon and Jeger, 1948; Dorde, McGhie and Kurzer, 1 9 4 9 ~ ) . These reactions also indicate that the hydroxyl is contained in a six-membered ring. One of the ethylenic linkages is readily hydrogenated and has been shown to be present as the grouping -CH = CMe,.
FIESER: Ours was killed 4 hours after injection, and this was only one rat. We want t o do a lot of experiments, allowing varying periods of incubation. Only then can we get data which can be interpreted. I just mentioned this as preliminary work. We are also doing the following kind of experiment. The skin of the rat is known to contain high amounts of 7-dehy~ocholesterol,and also Baumann a t Wisconsin has found that skin sterols of smaller animals contain up to 20-25 per cent lathosterol. So we’re going to administer our acetate, kill the rat, skin him, and work up the carcass and skin separately and see what we can find.
The arguments in favour of this rn are briefly as follows. From application of his generalized Molecular Rotation Difference Method, Klyne (1952) has concluded that rings A and B are trans fused and that the C, methyl group has the same configuration in space as the C,, methyl groups in steroids and the C, methyl group in the pentacyclic triterpenoids. The hydroxyl must be on the same side (/3) as the C, methyl group, on the basis of arguments adduced elsewhere. The methyl group at C,, is placed ,8 in order to explain the high degree of steric hindrance shown by the polar type hydroxyl a t Cl,.