G. Fodor
1967
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Abstract
Publisher Summary This chapter discusses experimental studies focusing on the tropane alkaloids. Phyllalbine, isolated from roots of Phylluntus discoides Muell. Arg. by J. Manil, was investigated chiefly by modern physical methods. Its molecular formula, C 16 H 21 O 4 N was corroborated by mass spectrometry. The NMR-spectrum showed the same signals as tropine and its esters; in particular, the triplet due to the C-3 proton at 5.25 δ is very similar to that of atropine. Pseudotropine esters, for example, tropacocaine show a quintuplet in almost the same region for the 3α-proton. The methoxyl group appeared at 3.94 ppm while the position of the signal of phenolic hydroxyl varied with the concentration and disappeared on deuteration. The IR-spectrum suggested the presence of a carbonyl joined to an aromatic nucleus so that a vanilloyl or isovanilloyltropan-3α-ol seemed very probable. Hydrolysis to tropine and vanillic acid completed the evidence. Structural elucidation of phyllalbine, valeroidine, and ecgoninols is discussed in detail, and total synthesis of meteloidine and oscine is described. The stereochemistry of the ring nitrogen in the tropanes is also discussed.