Chapter 7 The Tropane Alkaloids

作者: G. Fodor

DOI: 10.1016/S1876-0813(08)60203-1

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摘要: 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 modern physical methods. Its molecular formula, C 16 H 21 O 4 N corroborated mass spectrometry. The NMR-spectrum showed same signals as tropine and its esters; in particular, triplet due to C-3 proton at 5.25 δ is very similar that atropine. Pseudotropine esters, for example, tropacocaine show a quintuplet almost region 3α-proton. methoxyl group appeared 3.94 ppm while position signal phenolic hydroxyl varied with concentration disappeared deuteration. IR-spectrum suggested presence carbonyl joined an aromatic nucleus so vanilloyl or isovanilloyltropan-3α-ol seemed probable. Hydrolysis vanillic acid completed evidence. Structural elucidation phyllalbine, valeroidine, ecgoninols discussed detail, total synthesis meteloidine oscine described. stereochemistry ring nitrogen tropanes also discussed.

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