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Catalpa glycosides - II the structure of catalposide

✍ Scribed by J.M. Bobbitt; D.W. Spiggle; S. Mahboob; W. von Philipsborn; H. Schmid

Book ID: 104212533
Publisher: Elsevier Science
Year: 1962
Tongue: French
Weight: 408 KB
Volume: 3
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)70875-6

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✦ Synopsis

STRUCTURE Ia has recently2 been proposed for catalposide, the major glucoside of the genus Catalpa.

The assignment was based upon the following evidence. Reduction with lithium in liquid ammonia yielded bisdesoxyaucubin, XV (isolated as the tetraacetate) which was obtained in a similar 3 manner from aucubin. Catalposide and its saponification product, des-ehydroxybenzoylcatalposide, III (catalpo12) give crystalline acetates which were considered to be heptaacetates.

On the basis of chemical and NMR evidence, I, rather than Ia, is a preferred structure for catalposide. The chemical evidence will be presented first.

Catalposide has been shown' to form a dihydroderivative, V, a methyl ether, IV, and a dihydromethyl ether, VII. Both catalposide and dihydrocatalposide yield hexamesylates (hexamethansulfonates) and the corresponding methyl ethers yield pentamesylates. Thus, catalposide contains six hydroxyl groups rather than seven.2 In addition, catalposide takes up five moles of

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