Abstract
17β-Hydroxy-des-A-androst-9-en-5-one (II, R=OH), prepared fromtrans-1β-hydroxy-8-methyl-4, 5-(3′-methyl-4′-methoxybenzo)-hydrindane (I, R=CH3)′, has been converted intodl-9(II)-dehydrotestosterone (IV, R=OH) anddl-testosterone (IX) in very short sequences of steps, albeit in poor yields.
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Banerjee D K, Chatterjee S, Pillai C N and Bhatt M V 1956J. Am. Chem. Soc. 78 3769
Banerjee D K, Murthy P S N and Paul V 1967Tetrahedron Lett. 1879
Banerjee D K, Paul V, Balasubramanian S K and Murthy P S N 1964Tetrahedron 20 2487
Bhalla V K, Nayak U R and Dev S 1967J. Chromatogr. 26 54
Demaecker and Martin R H 1954Nature 173 266
Edward J T and Lawson N E 1970J. Org. Chem. 35 1426
Fujimoto G I 1951J. Am. Chem. Soc. 73 1856
Hajos Z G, Parrish D R and Olivero E P 1966Tetrahedron Lett. 6495
Hajos Z G, Micheli R A, Parrish D R and Olivero E P 1967J. Org. Chem. 32 3008
Hajos Z G, Parrish D R and Olivero E P 1968Tetrahedron 24 2039
Hartshorn M P and Jones E R H 1962J. Chem. Soc. 1312
Johnson W S Private Communication
Murthy P S N 1968, Ph. D. Thesis, Indian Institute of Science, Bangalore
Turner R B 1950J. Am. Chem. Soc. 72 579
Uskovic M, Iacobelli J, Philion R and Williams T 1966J. Am. Chem. Soc. 88 4538
Velluz L, Valls J and Nomine G 1965Angew. Chem. 77 185
Velluz L, Nomine J, Mathieu J, Toromanoff E, Bertin D, Bucourt R and Tessier J 1960Compt. Rend. 250 1293
Velluz L, Nomine G and Mathieu J 1960bAngew. Chem. 72 725
Velluz L, Mathieu J and Nomine G 1966Tetrahedron Suppl No. 8 Part 1 501
Vida J A and Gut M 1965J. Org. Chem. 30 1244
Woodward R B, Sondheimer F, Taub D, Heusler K and McLamore W M 1951J. Am. Chem. Soc. 73 2403
Woodward R B, Sondheimer F, Taub D, Heusler K and McLamore W M 1952J. Am. Chem. Soc. 74 4223
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Banerjee, D.K., Damodaran, K.M., Murthy, P.S.N. et al. Total synthesis ofdl-9(11)-dehydrotestosterone anddl-testosterone. Proc. Indian Acad. Sci., A (Chemical Sciences) 87, 239–246 (1978). https://doi.org/10.1007/BF03182138
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DOI: https://doi.org/10.1007/BF03182138