General synthetic strategy for clavaminols A, C and H

Thirupathi, Barla; Bharath, Yada; Mohapatra, Debendra K.

doi:10.3998/ark.5550190.p009.281

Cited by 2 publications

(2 citation statements)

References 29 publications

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“…Generally, the synthetic methods for the preparation of Clavaminol A and Xestoaminol C have been based on both chiral pool and asymmetric synthesis. The typical chiral starting materials involve alanine,, , , , serine, Garner aldehyde, carbohydrates and glycidol . Asymmetric synthesis utilizes Sharpless epoxidation,, , Sharpless dihydroxylation, Henry reaction, azidirination, hydrazination via “enamine catalysis” and anti ‐aminohydroxylation , .…”

Section: Introductionmentioning

confidence: 99%

Enantioselective Synthesis of Clavaminol A, Xestoaminol C and their Stereoisomers Exhibiting Cytotoxic Activity

et al. 2020

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The simple preparation of the natural sphingoid bases possessing cytotoxic activity – the marine drugs Clavaminol A and Xestoaminol C and all their unnatural stereoisomers – in high enantiomeric purity (ca. 95 % of major enantiomer) was described. The individual enantiomers were obtained by the utilization of asymmetric Henry reaction. The diastereomers of target compounds were separated by column chromatography after transformation into corresponding 2‐phenyloxazoline derivatives. The individual stereoisomers of Clavaminol A and Xestoaminol C were evaluated for antiproliferative activity in cancer cell lines (A‐549; Jurkat; SH‐SY5Y, MG‐63). From the obtained IC50 values is obvious, that the stereoisomers of Xestoaminol C are more potent inhibitors of cell proliferation than the stereoisomers of Clavaminol A. Further, it was found, that stereoisomers with syn‐configuration exhibited larger antiproliferative effects in comparison with the stereoisomers having anti‐configuration, in both sphingoid bases. Nevertheless, the values of IC50 found for individual enantiomers in each of the enantiomeric pairs are rather comparable implying a possibility of using racemic mixtures for induction of cytotoxicity.

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Section: Introductionmentioning

confidence: 99%

Enantioselective Synthesis of Clavaminol A, Xestoaminol C and their Stereoisomers Exhibiting Cytotoxic Activity

et al. 2020

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“…3,4 However, the reaction outcomes are often limited with respect to the achieved diastereoselectivities and occasionally require additional oxidation/reduction sequences to increase the overall yield of the desired diastereomer. [5][6][7] Furthermore, N-Boc protection most often results in the formation of rotameric mixtures, which render proper NMR analysis challenging. 8 Although the use of the sterically more hindered benzyl protecting group results in high diastereoselectivities, their removal requires reductive deprotection conditions, which are incompatible with unsaturated functionalities.…”

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confidence: 99%