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

ISBN-10: 0080865275

ISBN-13: 9780080865270

ISBN-10: 0124695035

ISBN-13: 9780124695030

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Extra info for Alkaloids: v. 3: Chemistry and Pharmacology

Sample text

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.

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


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