By R.H.F Manske, H.L. Holmes
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Extra info for Alkaloids: v. 3: Chemistry and Pharmacology
The desoxy bases, of the general structure XCVIII,have usually been prepared by transformation of the cinchona alkaloids into chlorides (XCVII)by phosphorus pentachloride and removal of the halogen in the latter by metalacid combinations (64,97, 134, 135, 136). It is reported that direct removal of the hydroxyl group is brought about by electrolytic reduction (132). XCVII XCVIII 24 RICHARD B. TURNER AND R. B. WOODWARD The desoxy compounds, like other similarly constituted substances, (cf. 9 (137).
24,2083 (1891)). The horimntal linea project forward, and the vertical onea, backward. 28 RICHARD B. TURNER AND I(. B. 3 of the cinchona alkaloids with that of asymmetric centers in other natural THEta H-(i-cH* CSHElr CXVI substancee (150). It also forms the basis for the particular space formulae used throughout our discussion. Should it become necessary to reverse the present conventions with regard to absolute configuration, each of our representations should be replaced by the corresponding mirror image.
WOODWARD further conclusion may be drawn that d of. the substances possess identical con$gurations at these centers. From the alkaloids, by more extensive degradation (60,147), or from meroquinene (64, 148), d-8-cincholoiponic acid (CV) i3 obtainable. This acid is unstable with respect to a stereoisomer, d-a-cincholoiponic acid, into which it is transformed when it is heated with aqueous potash (65). This result suggests that the 8-acid, and thence, the alkaloids themselves, possess the cis orientation of the groups attached to the piperidine ring.