title: Synthesis of ent-kaurane diterpene monoglycosides.
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.
authors.affiliation: Organic Chemistry Department, Global Research and Development, The Coca-Cola Company, One Coca-Cola Plaza, Atlanta, GA 30313, USA. vchaturvedula@na.ko.com
authors.forename: Venkata Sai Prakash
authors.initials: VS
authors.lastname: Chaturvedula
authors.forename: Josef
authors.initials: J
authors.lastname: Klucik
authors.forename: Mani
authors.initials: M
authors.lastname: Upreti
authors.forename: Indra
authors.initials: I
authors.lastname: Prakash
mesh_terms: D002384:Catalysis; D045786:Diterpenes, Kaurane / Q000138:chemical synthesis* / Q000737:chemistry*; D005502:Food; D009682:Magnetic Resonance Spectroscopy; D036625:Stevia / Q000737:chemistry; D013549:Sweetening Agents / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D045786:Diterpenes, Kaurane; D013549:Sweetening Agents; C570612:steviol 19-O-beta-D-glucopyranosiduronic acid; C515747:isosteviol; C012042:steviol