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Synthesis of ent-Kaurane Diterpene Monoglycosides
AbstractSynthesis of two ent-kaurane diterpene glycosides, steviol 19-O-β-D-glucopyranosiduronic acid (steviol glucuronide, 5), and 13-hydroxy ent-kaur-16-en-19-oic acid-β-D-glucopyranosyl ester (7) has been achieved from a common starting material, steviol, using phase transfer catalyst. Also, synthesis of an additional 17-nor-ent-kaurane glycoside, namely 13-methyl-16-oxo-17-nor-ent-kauran-19-oic acid-β-D-glucopyranosyl ester (10) was performed using the starting material isosteviol and similar synthetic methodology. Synthesis of all three steviol glycosides was performed using straightforward chemistry and their structures were characterized on the basis of 1D and 2D NMR as well as mass spectral (MS) data.
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Chaturvedula, V.S.P.; Klucik, J.; Upreti, M.; Prakash, I. Synthesis of ent-Kaurane Diterpene Monoglycosides. Molecules 2011, 16, 8402-8409.View more citation formats
Chaturvedula VSP, Klucik J, Upreti M, Prakash I. Synthesis of ent-Kaurane Diterpene Monoglycosides. Molecules. 2011; 16(10):8402-8409.Chicago/Turabian Style
Chaturvedula, Venkata Sai Prakash; Klucik, Josef; Upreti, Mani; Prakash, Indra. 2011. "Synthesis of ent-Kaurane Diterpene Monoglycosides." Molecules 16, no. 10: 8402-8409.