By R.H.F Manske, H.L. Holmes
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Additional resources for Alkaloids: Chemistry and Pharmacology, Volume 14
Carbon skeleton, the C-12 The unusual 17~-methyl-l8-nor-cholestane position of the second double bond, and the stereochemistry of veramine at C-25 were established from this correlation. As there is no identity between veralkamine (104), (which possesses a 16p-hydroxy group) and the diol (128), the only structural difference was in the configuration at C-16. The N-chloro derivative (129) of 128 recyclizes in contrast to the N-chloro derivative of veralkamine (116); therefore veramine has a 16a,17a structure of the spiroaminoketal side chain.
Acetylation of 148 and its N-methyldihydro derivative 152 yielded the N ’,O-diacetate 153 and the O-acetate 154, respectively. The negative molecular rotation increment of compound 152 after acetylation confirmed the a-orientation of the C-16 hydroxy group. Dihydrocyclokoreanine-A (152) and cyclovirobuxine-A (155) have different melting points although their PMR and I R spectra differ in minor points only. Therefore it was assumed that the difference between them was due to the opposite orientation of the C-3 dimethylamino group.
H RO R 96 97 98 R1 D - G ~ u CH,CO H H D-Glu H RO 99 100 R = CH,CO, A6*aa(a3) R =H HO 101 1. 23 STEROID ALKALOIDS 3. 2" in ethanol) was isolated from the green part of Veratrum Zobelianum (69). The mass spectrum of veralozidine exhibited a fragmentation pattern indicative of a 22,26-epiminocholestane skeleton. The UV spectrum of this alkaloid showed a maximum attributable to the C-N double bond. Veralozidine displayed I R absorption due to a hydroxy, a 3phydroxy-5-ene, and a C-N group. The PMR spectrum of veralozidine showed protons associated with the C-18, C-19, C-21, and C-27 methyl groups and a C-6 vinyl proton.
Alkaloids: Chemistry and Pharmacology, Volume 14 by R.H.F Manske, H.L. Holmes