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Synthesis of ent-Kaurane Diterpene Monoglycosides
Organic Chemistry Department, Global Research and Development, The Coca-Cola Company, One Coca-Cola Plaza, Atlanta, GA 30313, USA
* Author to whom correspondence should be addressed.
Received: 26 August 2011; in revised form: 28 September 2011 / Accepted: 29 September 2011 / Published: 3 October 2011
(This article belongs to the Special Issue Terpenoids
Abstract: Synthesis 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.
Keywords: ent-kaurane diterpene glycosides; nor ent-kaurane glycoside; steviol, isosteviol; synthesis; structure characterization; spectral 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.
Chaturvedula VSP, Klucik J, Upreti M, Prakash I. Synthesis of ent-Kaurane Diterpene Monoglycosides. Molecules. 2011; 16(10):8402-8409.
Chaturvedula, Venkata Sai Prakash; Klucik, Josef; Upreti, Mani; Prakash, Indra. 2011. "Synthesis of ent-Kaurane Diterpene Monoglycosides." Molecules 16, no. 10: 8402-8409.