By R.H.F. Manske and R.G.A. Rodrigo (Eds.)
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The 'H NMR spectrum of falaconitine was identical with mithaconitine except for the presence of the veratroy1 group instead of a benzoyl group. Comparison of these alkaloids to pseudaconitine (21),indaconitine (23),and pyrodelphinine (29)was made through a study of their 13CNMR spectra. 3 ppm) afforded evidence for the presence of a double bond between C-8 and C-15 in these new alkaloids. Further, the 13CNMR data indicated that these new alkaloids were similar to pseudaconitine (21)and indaconitine (23)except for the presence of the double bond between the C-8 and C-15 positions.
Since Marion and colleagues have correlated chasmanine with neoline and homochasmanine with chasmanine, the structures previously assigned for chasmanine (77) and homochasmanine (79) (50 and 52, respectively), must be reconsidered. Chasmanine and neoline were converted to 8,14-di0-methyl chasmanine and 1,8,14-tri-O-methylneoline(56), respectively, 20 S . WILLIAM PELLETIER A N D N A R E S H V. M O D Y ......... CH 49 Chasmanine-,$ " ,~? 47 Neoline I ....... C2H,--- - - N '. OCH, OCH, OCH, 56 by treatment of each alkaloid with sodium hydride and methyl iodide in refluxing dioxane.
Miyabei Nakai, a plant native to Hokkaido, Japan. On the basis of chemical studies, they reported that base D contains an N-methyl, a benzoxyl, an acetoxyl, a hydroxyl, and four methoxyl groups. On treatment with acetyl chloride, base D gave a monoacetate, mp 188-190". The data indicated that base D has the same empirical formula and functional groups as delphinine (31), but differs from delphinine by the mixture-melting point (mmp) and infrared spectra. On the basis of an infrared analysis and chemical studies, Katsui postulated that isodelphinine is a C-14 epimer of delphinine.
Chemistry and Physiology by R.H.F. Manske and R.G.A. Rodrigo (Eds.)