Reactions of epoxides—V
作者： J.W. Blunt , M.P. Hartshorn , D.N. Kirk
DOI: 10.1016/S0040-4020(01)82227-4
关键词:
摘要: Abstract 5,6,α-Epoxy-6β-methyl-5α-cholestane, like its 3β-acetoxy derivative, undergoes rearrangement with boron trifluoride to give the 5β-methyl-A-homo-B-nor-4a-ketone. The 3-deoxy-4a-ketone, however, a further 5-methyl-5β-cholestan-6-one. 3β-Acetoxy-5,6β-epoxy-6α-methyl-5β-cholestane reacts rapidly fluorohydrin, which suffers slower both 5β-methyl-A-homo-B-nor-4a-ketone and 3β-acetoxy-5-methyl-5α-cholestan-6-one. In contrast, 3-deoxy 5β,6β-epoxide gives 6-methyl-cholesta-3,5-diene, 5-acetyl-B-nor-5β-cholestane, 5-methyl-5α-cholestan-6-one.
elsevier.com
sci-hub.se 参考文章(11)
Herbert O. House, The Rearrangement of α,β-Epoxy Ketones. III. The Intramolecular Nature of the Rearrangement Journal of the American Chemical Society. ,vol. 78, pp. 2298- 2302 ,(1956) , 10.1021/JA01591A073
Jehan F. Bagli, Peter F. Morand, R. Gaudry, Synthetic Studies on C-19 Oxygenated Pregnanes Journal of Organic Chemistry. ,vol. 28, pp. 1207- 1217 ,(1963) , 10.1021/JO01040A010
William Moffitt, R. B. Woodward, A. Moscowitz, W. Klyne, Carl Djerassi, Structure and the Optical Rotatory Dispersion of Saturated Ketones Journal of the American Chemical Society. ,vol. 83, pp. 4013- 4018 ,(1961) , 10.1021/JA01480A015
David J. Goldsmith, The Cyclization of Epoxyolefins: The Reaction of Geraniolene Monoepoxide with Boron Fluoride Etherate Journal of the American Chemical Society. ,vol. 84, pp. 3913- 3918 ,(1962) , 10.1021/JA00879A022
Jehan F. Bagli, Peter F. Morand, R. Gaudry, Chromic Acid Oxidation of Organoboranes. A Convenient Route to 6-Keto Steroids Journal of Organic Chemistry. ,vol. 27, pp. 2938- 2940 ,(1962) , 10.1021/JO01055A519
David N. Kirk, Vladimir Petrow, 900. Modified steroid hormones. Part XIX. Steroidal 5β-methyl-A-homo-B-nor-4,4a-unsaturated ketones. A new class of hormone analogue Journal of The Chemical Society (resumed). pp. 4657- 4663 ,(1960) , 10.1039/JR9600004657
C. W. Shoppee, R. H. Jenkins, G. H. R. Summers, 329. Steroids and Walden inversion. Part XXXIX. The halogenation of 5α-cholestan-6-one and the pyrolysis of 5-chloro-5α-cholestan-6-one J. Chem. Soc.. ,vol. 0, pp. 1657- 1663 ,(1958) , 10.1039/JR9580001657
H. B. Henbest, T. I. Wrigley, 960. Aspects of stereochemistry. Part IX. The formation of fluorohydrins from the cholesterol 5 : 6-epoxides and boron trifluoride–ether complex Journal of The Chemical Society (resumed). pp. 4765- 4768 ,(1957) , 10.1039/JR9570004765
N. Elenkova, G. Todorova, Eine Methode zur amperometrischen Bestimmung von Arsen(III) Analytica Chimica Acta. ,vol. 29, pp. 364- 365 ,(1963) , 10.1016/S0003-2670(00)88629-8
B. Ellis, D. N. Kirk, V. Petrow, B. Waterhouse, D. M. Williamson, 571. Modified steroid hormones. Part XVII. Some 6-methyl-4,6-dien-3-ones Journal of The Chemical Society (resumed). pp. 2828- 2833 ,(1960) , 10.1039/JR9600002828