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NMR assignments and absolute configuration of kauranoids

✍ Scribed by R. X. Tan; W. Z. Wang; S. X. Wu; L. Yang

Publisher
John Wiley and Sons
Year
1995
Tongue
English
Weight
457 KB
Volume
33
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

A new ent‐kaurane diterpenoid glycoside has been shown to be the main sweetening constituent of the traditional medicines Aster tongolensis and A. ageratoides native to China. This study involved the total ^1^H and ^13^C spectral assignment of the compound and its degraded product by means of two‐dimensional NMR techniques (COSY, NOESY, HETCOR and TOCSY) and resulted in unambiguous spectral assignments, particularly in the heavily convoluted regions of the spectra. Concerning the absolute stereochemistry, the sweetener was determined to be (4__R__,5__S__,8__S__,9__S__,10,13__R__)‐16,17‐dihydroxykauran‐19‐oic acid β‐D‐glucopyranosyl ester through a combination of circular dichroism and 2D NMR techniques.

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