Organic Chemistry - Semi-synthetic diversification of Coronarin D, a Labdane Diterpene, under Ugi Reaction Conditions  

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  • Semi-synthetic diversification of Coronarin D, a Labdane Diterpene, under Ugi Reaction Conditions
Semi-synthetic diversification of Coronarin D, a Labdane Diterpene, under Ugi Reaction Conditions

Kollery Veena, Murikkinthara Taniya, Jaice Ravindran, Arun Kumar Thangarasu, Sulochana Priya & Ravi Shankar Lankalapalli*

The prevalence of 5-hydroxydihydrofuran-2(3H)-one moiety in natural products is exploited for the first time using coronarin D, a labdane diterpene, to afford Ugi reaction product 1a and interrupted Ugi product 2a. The potential of the Ugi reaction was further extended to L-phenylalanine, 2-aminopyridine, and Dglucosamine, which afforded Ugi reaction products 3a–f, 4, and 5a–d, respectively. Cytotoxicity studies in RAW cells reveal that compounds 3e and 5b were non-toxic up to 50 mM, and these compounds were able to reduce the LPS stimulated NO production in RAW cells in par with the standard anti-inflammatory drug dexamethasone.

Natural Product Research 2020.  DOI: 10.1080/14786419.2020.1782406.

 

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