By R.H.F Manske, H.L. Holmes
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Extra info for Alkaloids: v. 3: Chemistry and Pharmacology
TURNER AND R. B. WOODWARD CHO (Di)hydroxyphcnylalanime OyT 1.
This goal was reached in 1944 (233). The starting point for the synthetic work was 7-hydroxyieoquinoline (CXCV)which was obtained by condensation of m-hydroxybenzaldehyde and aminoacetal, followed by cyclization with sulfuric acid. The carbon atom required for completion of the homomeroquinene skeleton was introduced by condensation of CXCV with formaldehyde and piperidine. 7-Hydroxy-8-piperidinomethylisoquinoline(CXCVI) was obtained in this way, and was smoothly converted into 7-hydroxy-S-rnethylisoquinoline (CXCVII)by treatment with methanolic sodium methoxide at 220'.
Conversion of the phenolic base to the corresponding amine (C) by the Bucherer reaction, followed XCIX C by diazotization and reduction by hypophoaphorous acid, led to dihydrocinchonine (138). In a similar may, cupreine was converted to cinchonidine. These transformations proved rigorously the long-assumed relationships, 6'-methoxycinchonine = quinidine, and 6'-methoxycinchonidine = quinine. e. l. l to give quaternary salts (139). 1-oxides (140-142). It is of some interest that the vinyl group in quinine N.
Alkaloids: v. 3: Chemistry and Pharmacology by R.H.F Manske, H.L. Holmes