Abstract
Corticosteroids are products of high industrial and commercial importance. There are dozens of different synthesis published for all of them. Some are coming from academia and some from industry. Here, industrial processes for the synthesis of prednisone, prednisolone, hydrocortisone, dexamethasone, betamethasone, and methylprednisolone are described. The starting material is diosgenin and the desired molecules are reached due to a good combination of chemistry and biotechnology that was developed along the second part of the twentieth century.
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References
Hench PS, Kendall EC, Slocumb CH, Polley HF (1949) The effect of a hormone of the adrenal cortex (17-hydroxy-11-dehydrocorticosterone: compound E) and of pituitary adrenocorticotropic hormone on rheumatoid arthritis. Ann Rheum Dis 8:97–104
Marker RE, Rohrmann E (1940) Sterols. LXXXVIII. Pregnanediols from sarsasapogenin. J Am Chem Soc 62:518–520
Marker RE, Tsukamoto T, Turner DL (1940) Sterols. C. Diosgenin. J Am Chem Soc 62:2525–2532
American Chemical Society, Sociedad Química de Mexico (1999) https://www.acs.org/content/dam/acsorg/education/whatischemistry/landmarks/progesteronesynthesis/marker-degradation-creation-of-the-mexican-steroid-industry-by-russell-marker-commemorative-booklet.pdf
Oppenauer RV (1937) Eine methode der dehydrierung von sekundaren alkoholen zu ketonen. I, zur herstellung von sterinketonen und sexualhormonen. Recl Trav Chim Pays-Bas 56:137–144
Peterson DH, Murray HC (1952) Microbiological oxygenation of steroids at carbon-11. J Am Chem Soc 74:1871–1872
Peterson DH, Murray HC (1952) Oxygenation of steroids by Mucorales fungi. US Patent US2602769
Peterson DH, Murray HC, Eppstein SH, Reineke LM, Weintraub A, Meister PD, Leigh HM (1952) Microbiological transformation of steroids. I. Introduction of oxygen at carbon-11 of progesterone. J Am Chem Soc 75:5933–5936
Stork G, Ringold HJ, Sondheimer F, Rosenkranz G (1959) Process for the production of 20-Keto-21-Iodo steroids. US Patent US2874154
Joly R, Jolly J (1961) Procédé d'acétoxylation de stéroïdes en 21 par l'intermédiaire de dérivés diiodés. French patent FR1243528
Burn D, Kirk DN, Petrow V (1960) A new reagent for the preparation of Δ1,4- and Δ1,4,6-steroidal ketones. Proc Chem Soc 14
Meystre C, Frey H, Voser W, Wettstein A (1956) Gewinnung von 1;4-Bisdehydro-3-oxo-steroiden. Helv Chim Acta 34:734–742
Nobile A (1958) Process for production of dienes by Corynebacteria. US Patent US2837464
Herzog HL, Payne CC, Hughes MT, Gentles MJ, Hershberg EB, Nobile A, Charney W, Federbush C, Sutter D, Perlman PL (1962) Microbiological transformations of steroids. X. 1-Dehydro analogs of cortical steroids. Tetrahedron 18:581–589
Oliveto EP, Rausser R, Weber L, Shapiro E, Gould D, Hershberg EB (1956) 11-Oxygenated steroids. XVI. The preparation of Hydrocortisone from cortisone acetate. J Am Chem Soc 78:1736–1738
Slates HL, Wendler NL (1959) Reaction of diazomethane with Δ16-21-keto steroids. J Am Chem Soc 81:5472–5475
Gardner JN, Carlon FI, Gnoj O (1968) A one-step procedure for the preparation of tertiary α-ketols. J Org Chem 33:3294–3297
Gardner JN (1967) Method for introducing an oxygen function into a steroid molecule containing a keto group. US Patent US3356696
Suvorov NN, Sokolova LV, Makarov NV (1960) Reaction of methyl magnesium iodide with ketoxides of steroids. Izvestiya Academii Nauk SSRR, seriya khimicheskaya 2257–2258
Sciaky R (1961) Synthesis of 16β-methyl-17α-acetoxyprogesterone. Gaz Ch Ital 91:562–570
Amiard G, Torelli V, Cerede J (1963) Process of preparation of β-Methasone. US Patent US3104246
Fu X, Tann CH, Thiruvengadam TK (2001) Process improvements in the synthesis of corticosteroid 9,11β-epoxides. Org Process Res Dev 5:376–382
Hanc O, Capek A, Kakac B (1961) Microbiological transformations of steroids. XV. Transformation of steroid S (Reichstein) by Absidia orchidis 310. Folia Microbiol 6:392–397
Hanc O, Capek A, Tadra M (1962) Microbiological transformation of steroids. XVI. Preparation of cortisol and cortisone from 17alpha-hydroxycortexone with the use of microbial hydroxylation with the aid of Absidia orchidis 310. Cesk Farm 11:181–185
Wix G, Weisz E, Albrecht K, Varga M, Kassazan B, Doczi B (1966) Verfahren zur Herstellung von Hydrocortison. Austrian Patent AT 248630
Breuker E, Hamann KH, Singer S Wagner B (1968) Process for the manufacture of Δ4-Pregnene-11β and 11α,17α, 21-triol-3,20-Diones. British Patent GB 1100505
Bowers A, Ringold HJ (1958) Synthesis of 6a-Methyl-21-desoxycortisone. A new route to 6a-Methylcortisone. J Am Chem Soc 80:3091–3093
(1962) Cyclopentanophenanthrene derivatives. British Patent GB 897732
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Herráiz, I. (2017). Chemical Pathways of Corticosteroids, Industrial Synthesis from Sapogenins. In: Barredo, JL., Herráiz, I. (eds) Microbial Steroids. Methods in Molecular Biology, vol 1645. Humana Press, New York, NY. https://doi.org/10.1007/978-1-4939-7183-1_2
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DOI: https://doi.org/10.1007/978-1-4939-7183-1_2
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