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. 2011 Oct 3;16(10):8402-9.
doi: 10.3390/molecules16108402.

Synthesis of ent-kaurane diterpene monoglycosides

Venkata Sai Prakash Chaturvedula  1 , Josef Klucik, Mani Upreti, Indra Prakash
Affiliations

Synthesis of ent-kaurane diterpene monoglycosides

Venkata Sai Prakash Chaturvedula et al. Molecules. .

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.

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Figures

Scheme 1
Scheme 1
Synthesis of steviol acetate (2).
Scheme 2
Scheme 2
Synthesis of steviol glucuronide (5).
Scheme 3
Scheme 3
Synthesis of 13-hydroxy ent-kaur-16-en-19-oic acid-β-D-glucopyranosyl ester (7).
Scheme 4
Scheme 4
Synthesis of 13-methyl-16-oxo-17-nor-ent-kauran-19-oic acid-β-D-gluco-pyranosyl ester (10).
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References

    1. Brandle J.E., Starrratt A.N., Gijen M. Stevia rebaudiana: Its agricultural, biological and chemical properties. Can. J. Plant Sci. 1998;78:527–536. doi: 10.4141/P97-114. - DOI
    1. Chaturvedula V.S.P., Rhea J., Milanowski D., Mocek U., Prakash I. Two minor diterpene glycosides from the leaves of Stevia rebaudiana. Nat. Prod. Commun. 2011;6:175–178. - PubMed
    1. Chaturvedula V.S.P., Mani U., Prakash I. Diterpene glycosides from Stevia rebaudiana. Molecules. 2011;16:3552–3562. doi: 10.3390/molecules16053552. - DOI - PMC - PubMed
    1. Chaturvedula V.S.P., Prakash I. A new diterpenoid glycoside from Stevia rebaudiana. Molecules. 2011;16:2937–2943. doi: 10.3390/molecules16042937. - DOI - PMC - PubMed
    1. Chaturvedula V.S.P., Prakash I. Structures of the novel diterpene glycosides from Stevia rebaudiana. Carbohydr. Res. 2011;346:1057–1060. doi: 10.1016/j.carres.2011.03.025. - DOI - PubMed

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