C-22 ketals related to the sapogenins

作者: H. Hirschmann , Frieda B. Hirschmann

DOI: 10.1016/0040-4020(58)80020-4

关键词:

摘要: Abstract Reduction of 5,6-dihydrokryptogenin diacetate with Raney nickel in ethanol reduced the 16-ketone group and gave a mixture 22-ethyl ketal hemiketal. Both undergo elimination reactions very readily to yield Δ22-bond isomer pseudotigogenin diacetate. The conversions are reversible catalyzed by acetic acid neutral solution calcium sulfate other surfaces. Alkaline hydrolysis followed cyclization converted both Δ22-olefin tigogenin. relative stabilities epimers at C-22 discussed related stereo-chemistry sapogenins cyclopseudosapogenins.

参考文章(27)
Erich. Heftmann, Alma.Levant. Hayden, Paper chromatography of steroid sapogenins and their acetates. Journal of Biological Chemistry. ,vol. 197, pp. 47- 55 ,(1952) , 10.1016/S0021-9258(18)55652-0
Farrington Daniels, Preston L. Veltman, The Decomposition of Ethyl Bromide and the Collision Theory of First‐Order Reactions Journal of Chemical Physics. ,vol. 7, pp. 756- 766 ,(1939) , 10.1063/1.1750522
C. R. Eddy, M. E. Wall, M. K. Scott, Catalog of Infrared Absorption Spectra of Steroidal Sapogenin Acetates Analytical Chemistry. ,vol. 25, pp. 266- 271 ,(1953) , 10.1021/AC60074A016
R. K. Callow, P. N. Massy-Beresford, 903. The stereochemistry of the side-chain of the steroidal sapogenins : configuration at C(22) of normal and iso-sapogenins Journal of The Chemical Society (resumed). pp. 4482- 4488 ,(1957) , 10.1039/JR9570004482
ROBERT S. MINER, EVERETT S. WALLIS, Molecular Rearrangements in the Steroids. XIII. The Non-reductive Scission of Rings E and F of the Steroidal Sapogenins Journal of Organic Chemistry. ,vol. 21, pp. 715- 720 ,(1956) , 10.1021/JO01113A001
D. H. R. Barton, J. E. Page, C. W. Shoppee, 68. Infrared absorption of halogeno-steroids Journal of The Chemical Society (resumed). pp. 331- 336 ,(1956) , 10.1039/JR9560000331
William Tarpley, Cecelia Vitiello, Infrared Spectra of Steroids. II. The Influence of the Solvent on Carbonyl Frequency Correlations Applied Spectroscopy. ,vol. 9, pp. 69- 77 ,(1955) , 10.1366/000370255774634070
R. K. Callow, D. H. W. Dickson, J. Elks, R. M. Evans, V. H. T. James, A. G. Long, J. F. Oughton, J. E. Page, Stereochemistry of the side-chain of the steroidal sapogenins: new isomers of the normal- and iso-sapogenins Journal of the Chemical Society (Resumed). pp. 1966- 1977 ,(1955) , 10.1039/JR9550001966
Monroe E. Wall, Henry A. Walens, Steroidal Sapogenins. XXVII. Preparation and Properties of 20-Isosapogenins2 Journal of the American Chemical Society. ,vol. 77, pp. 5661- 5665 ,(1955) , 10.1021/JA01626A058
D. H. R. Barton, A. J. Head, R. J. Williams, 354. Stereospecificity in thermal elimination reactions. Part III. The pyrolysis of (–)-menthyl benzoate J. Chem. Soc.. ,vol. 0, pp. 1715- 1719 ,(1953) , 10.1039/JR9530001715