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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In this general connection, it should be pointed out that exceptionally complete optical information is available for the cinchona alkaloids and their derivatives, and that this data has not infrequently been of value in providing intimations of stereochemical relationships, the correctness of which has subsequently been rigorously demonstrated by chemical means. The optical superposition rule is not quantitatively obeyed, but qualitative agreement is good, with certain notable exceptions (for example, the cinchona bromides).

N-Acetyl-10-aininodihydrohomomeroquineneethyl ester (CCII)was converted into N-acetyl-10-trimethylammoniumdihydrohomomeroquinene ethyl ester iodide (CCIV)by treatment with methyl iodide and potsssium carbonate. With 60% potassium hydroxide elimination occurred according to the Hofmann rule and, after treatment with potassium cyanate, homomeroquinene (CCV)was isolated from the reaction mixture as the N-uramido derivative. Regeneration of the homomeroquinene was accomplished by hydrolysis with dilute acid, and in this way, eis-ddhomomeroquinene was obtained.

2 by the spacially apposite hydroxyl group (CCXV). The reduction of the more highly oxygenated alkaloid to cinchonamine becomes readily R R H CCXIV ccxv explicable when it is considered that the grouping CCXVI may be reduced directly, or as the ring-chain tautomeric system (CCXVII), and THEl CHEMISTRY OF THlD CINCHONA ALKALOIDS 53 that the resulting 6-hydroxydihydroindole will suffer ready lw of water, with aromatiration to an indole derivative. I =Y--r-? CCXVI I N=C OH 1 1 1 CCXVII The structure CCXIII provides a satisfactory basis for the interpm tation of other transformations of quinamine.

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