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Updated: Jul 26, 2025

Hierarchical and Programmable One-Pot Oligosaccharide Synthesis
Published on: September 6, 2019
Divergent access to a novel 3,4-diaminophytosphingosine-like ceramide via sequential Overman rearrangement
Martin Fábian1, Michaela Novotná1, Jana Špaková Raschmanová1
1Institute of Chemical Sciences, Department of Organic Chemistry, P.J. Šafárik University, Moyzesova 11, 040 01, Košice, Slovak Republic.
Abstract:
A straightforward approach to a novel phytosphingosine-like ceramide has been accomplished. The cornerstone features of this divergent synthesis are a cascade Overman rearrangement of tris(imidate) to introduce three desired stereogenic centres via sequential chirality transfer and an effective olefin cross-metathesis to install a long side chain. The final unusual phytoceramides were evaluated for their capacity to inhibit the proliferation of cancer cell lines. The preliminary results revealed that compound 21 exhibits promising anticancer activity against HeLa and HCT-116 cells as well as the excellent selectivity in cytotoxicity (malignant vs non-malignant cell lines).
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