• Abstract
• Full-Text PDF [464 KB]

• Article Statistics
• PubMed/Medline
• Google Scholar
• Order Reprints

• Cite this article
• Export to BibTeX
• Export to EndNote

• [+] on DOAJ
• Chaturvedula, V
• Klucik, J
• Upreti, M
• Prakash, I
• [+] on Google Scholar
• Chaturvedula, V
• Klucik, J
• Upreti, M
• Prakash, I
• [+] on PubMed
• Chaturvedula, V
• Klucik, J
• Upreti, M
• Prakash, I

•  CiteULike
•  Facebook
•  Mendeley
•  Twitter

This article is

• freely available
• re-usable

Molecules 2011, 16(10), 8402-8409; doi:10.3390/molecules16108402

Article

Synthesis of ent-Kaurane Diterpene Monoglycosides

Venkata Sai Prakash Chaturvedula* , Josef Klucik, Mani Upreti and Indra Prakash

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)

Download PDF Full-Text [464 KB, uploaded 3 October 2011 09:46 CEST]

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

Article Statistics

Cite This Article