Alkaloids: v. 3: Chemistry and Pharmacology by R.H.F Manske, H.L. Holmes

By R.H.F Manske, H.L. Holmes

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A large number of O-chloro and 9-bromo bases has been prepared by the action of phosphorus halides on the various alkaloids (11-14,56,97, 134, 135, 151, 166, 167). It seems probable that the replacement of hydroxyl by halogen in these reactions takes place with inversion. 9 (97). In contrast, treatment of the halides with silver salts in neutral hydroxylic media results in smooth formation of substances of the hetero series (cf. Section 11, 1, d). 9 would be transformable to geometrically isomeric anhydro compounds (cf.

In the course of these investigations Pasteur achieved one of the greatest initial triumphs of stereochemistry, by showing that racemic acids could be resolved through combination with asymmetric alkaloidal bases. He also made the observation, which was to be of fundamental importance in studies on the structure, stereochemistry, and synthesis of the cinchona alkaloids, that the bases were convertible to isomeric substances, now known as toxines, and first classified the natural alkaloids on the basis of their optical properties.

Reactions had been found which served for the condensation of such components, and for the transformation of the resulting toxines into natural alkaloids. The key stage of the final effort was the preparation of dl-homocincholoipon in sufficient quantity for resolution, which was oarried out through the &-tartrates of the corresponding ethyl ester. The d t i n g (+)-homocincholoipon ester was converted into dihydroquinotoxine, and thence, by way of the C-bromo derivative, into dihydroquinidinone.

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