By R.H.F Manske, H.L. Holmes
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Extra info for Alkaloids: v. 3: Chemistry and Pharmacology
CXVII CXVIII 2. 9 of cinchonhe is removed, a desoxy base (CXIX) is obtained, which is isomeric with that derived in a similar fashion from cinchonidine (134, 151). 8. Quinine and quinidine me similarly related. 8 may be deduced from the circumstance that cinchonine and quinidine are convertible into cyclic ethers (CXX) (cf. Section 11, 2, a). No similar changes can be brought about with quinine and cinchonidine. 10 bonds are in the cis relationship, we may assign the structures CXXI to cinchonine and quinidine, and CXXII to cinchonidine and quinine (152).
Footnote, p. 27). CH: I E-C-NHCH: H-C-NHCH: ’i”: I I HO--~-H H-~-OH I Ph Ph CXXVII CXXVIII Now, epiquinine is a stronger base than quinine (97,162), and $-ephedrine is more strongly basic than ephedrine (163). From thia analogy, epiquinine may be assigned structure CXXX. It should be pointed out that this argument does not rest entirely on a purely formal basis. Inspection of models shows that the formation of a qwrsi ring involving --OH and -NRt in either ephedrine (CXXVII) or quinine (CXXIX) is strongly opposed, in the first case by interference between the bulky methyl and phenyl groups, and in the latter by similar repulsion between the quinoline and quinuclidine systems.
WOODWARD further conclusion may be drawn that d of. the substances possess identical con$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.
Alkaloids: v. 3: Chemistry and Pharmacology by R.H.F Manske, H.L. Holmes