By R.H.F Manske, H.L. Holmes
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Extra resources for Alkaloids: Chemistry and Pharmacology, Volume 14
Similarly, hydrolysis of 180 furnished cycloprotobuxoline-C (185). It was postulated that the ease of hydrolysis of N-benzoylcycloprotobuxolines might be attributable to the effect of a neighboring hydroxy group. To verify this assumption 185 was treated with phosgene, whereupon the oxazolidone 45 1. STEROID ALKALOIDS &2i3 R2R1O.. &c:H3 N ' " CH,' 179 180 182 184 185 188 CH,/ R R' R2 H CH, C,H5C0 H CH, CH, H C6H5C0 C6H5C0 C6H5C0 H H C,H,CO H H H H COCH, ,' 181 183 R R =H = C6H5C0 186 was formed.
On the basis of these data and those obtained from the mass spectrum the structural formula of buxiramine-D is probably 178. A proof of this assignment is desirable. 178 c. N- Benxoylcycloprotobuxoline-D and N-benxoylcycloprotobuxoline-C. N-Benzoylcycloprotobuxoline-D (179) and N-benzoylcyclosempervirens ( 8 t h ) . protobuxoline-C (180) were obtained from BUXUS The PMR spectrum of 179 indicated an N-methyl group with restricted internal rotation, one N-methyl group, one proton adjacent to a hydroxyl, five aromatic protons, and a cyclopropyl methylene; a n amide was inferred from the I R spectrum.
7' in methanol) has been found in Veratrum lobelianum. The IR spectrum of this alkaloid showed the absorption characteristic of an ester and a C-N group (68). Acid hydrolysis of 96 yielded veralozidine (97) and compound A (98). D-Glucose has been identified chromatographically in the neutral portion of the hydrolysis product. The saponification of veralozine gave compound A and acetic acid. Since veralozine did not give a J. TOMKO AND z. VOTICKY 22 precipitate with digitonin, it was considered that the glucose is bound in the C-3 position.