Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2016, Issue 27, Pages 4607-4610Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201600746
Keywords
Fatty acids; Homologation; Alkynes; Reduction; Oxidation; Inhibitors
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Funding
- Fonds der Chemischen Industrie (FCI)
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A flexible and efficient synthesis of the potent human topoisomerase inhibitor (5Z,9Z)-eicosa-5,9-dienoic acid was explored; the presented method represents a generally applicable approach towards demospongic acids and related natural products. Key steps of the synthesis involve chemoselective hydroboration, Corey-Fuchs alkynylation, Z-selective Lindlar reduction, tetrapropylammonium perruthenate catalyzed direct oxidation of a primary alcohol to the corresponding acid, and Arndt-Eistert homologation. Thus, the total synthesis of (5Z,9Z)-eicosa-5,9-dienoic acid was achieved in 10 steps in an overall yield of 20%.
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