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Journal Article

A Sphingolipid Fatty Acid Constituent Made by Alkyne trans-Hydrogenation: Total Synthesis of Symbioramide

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Radkowski,  Karin
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Fürstner,  Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Radkowski, K., & Fürstner, A. (2022). A Sphingolipid Fatty Acid Constituent Made by Alkyne trans-Hydrogenation: Total Synthesis of Symbioramide. Advanced Synthesis & Catalysis, 364(19), 3342-3347. doi:10.1002/adsc.202200540.


Cite as: https://hdl.handle.net/21.11116/0000-000B-5774-1
Abstract
A scalable approach to (2R)-hydroxyoctadec-3-enoic acid ((−)-2) is reported, which is the fatty acid constituent of numerous sphingolipids of biological significance. Key to success was the chemoselective trans-hydrogenation of a functionalized propargylic alcohol precursor with [Cp*RuCl]4 as the catalyst, followed by lipase-catalyzed resolution of the racemic product. (−)-2 then served the shortest total synthesis of the marine natural product symbioramide known to date.