Reduction of andrographolide and its stereostructure by NMR and X-ray study

Natural Product Research
Deepika Singh, Prabir K Chaudhuri

Abstract

Andrographolide (1) on asymmetric reduction with nickel boride in situ led to the identification of a product as 12,13 R-dihydroandrographolide (3) in de (>96%). The structure and stereochemistry of compound 3 were established by NMR study and confirmed by X-ray crystallographic analysis. β-Substituent of γ-butyrolactone in andrographolide exerted diastereomeric selectivity in reduction. Neoandrographolide (2) under similar condition yielded 5.

References

Aug 25, 2004·Bioorganic & Medicinal Chemistry Letters·Srinivas NanduriVenkateswarlu Akella
Jan 20, 2007·Phytochemistry·Srinivasa Rao JadaJohnson Stanslas
Apr 13, 2007·Bioorganic & Medicinal Chemistry·Hai-Wei XuHong-Min Liu
Jan 21, 2010·Journal of Agricultural and Food Chemistry·Wen-Wan ChaoBi-Fong Lin

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Citations

Oct 3, 2014·Natural Product Reports·James R Hanson
Jun 21, 2019·Natural Product Research·Sudhakar MokenapelliPrasad Rao Chitneni

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Methods Mentioned

BETA
NMR
X-ray

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