By R.H.F Manske, H.L. Holmes
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Extra resources for Alkaloids: v. 3: Chemistry and Pharmacology
Hydrolysis and decarboxylation of the resulting substituted malonate afforded tetrahydropyranyl-4-aceticacid (CLIV). Bouveault OS0,CJI' CHsCOOH 6 - 0 -0 CLII CLV CLIII CLVI CLIV CLVII reduction of this material (as the ester) followed by treatment with fuming hydrobromic acid furnished 3-(2-bromoethyl)-l,5-dibromopen- 40 RICHARD B. TURNER AND R. B. WOODWARD tane (CLVI), which was converted into quinuclidine (CLVII) by the action of ammonia in methanol. Various modificationa of this procedure were also successfully pursued.
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. 48 RICHARD B. TURNER AND R. B. WOODWARD Catalytic hydrogenation of the carbonyl group in the presence of palladium gave dihydroquinine, identical in all respects with the naturally occurring alkaloid.
9 would be transformable to geometrically isomeric anhydro compounds (cf. Section 11, 1, b). In fact, possibly for steric reasons, only one product is ordinarily obtained; the isolation of an anhydro base isomeric g t h dihydrocinchene has been reported, but the product was impure and incompletely characterized (97). 4. DIRECTINTERCONVERSIONS When quinine is subjected to the action of potassium hydroxide in hot amyl alcohol, a mixture of the four stereoisomeric bases, quinine, epiquinine, quinidine and epiquinidine, is obtained (168,169).
Alkaloids: v. 3: Chemistry and Pharmacology by R.H.F Manske, H.L. Holmes