Chemistry and Physiology by R.H.F. Manske (Eds.)

By R.H.F. Manske (Eds.)

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Sample text

C . Daphnilactone-A ................................................ D . Daphnilactone-B ................................................ E . Yuzurimine-Type Alkaloids ....................................... F . Alkaloids of Undetermined Structure ............................... I11. Chemistry ......................................................... A. Zinc Reduction .................................................. B . Anti-Bredt’s Rule Imine ..........................................

The reduction product of dihydrolysergic acid amide, 6-methyl8~-arninomethyl-lOa-ergoline proved to be a very fruitful starting material for the development of new active derivatives (108). Acetylation of its aminomethyl group led t o 6-methyl-8P-acetylaminomethylergoline (70) called Uterdina. This compound has a H O specific oxytoxic activity, comparable with that of ergometrine or methylergometrine (109, 110). Furthermore its toxicity is distinctly lower, the side effects being almost nonexistent.

The spectral data 2. THE DAPHNIPHYLLUM ALKALOIDS 59 of this alkaloid are quite different from those of daphniphylline (l),one of the main alkaloids. ,(EtOH) E , 7400 (end absorption); vmax 3490, 1744, 1735, and 1722 cm-l; NMR signals are cited in Table 1111 ( 2 4 ) . Chemical properties of yuzurimine are also fully consistent with the structure 43 (26). 66 ( l H , s) CDC1,. D,O. primary and secondary hydroxyl groups are sterically close t o each I I other. Furthermore, the presence of HO-C-N- grouping in 43 is also supported, as follows.

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