Synthesis of an electrophilic keto-tetraene 15-oxo-Lipoxin A4 methyl ester via a MIDA boronate |
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| Authors: | Steven R Woodcock Stacy G Wendell Francisco J Schopfer Bruce A Freeman |
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| Institution: | Department of Pharmacology and Chemical Biology, University of Pittsburgh, Pittsburgh, PA 16260, USA |
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| Abstract: | 15-oxo-Lipoxin A4 (15-oxo-LXA4) has been identified as a natural metabolite of the fatty acid signaling mediator Lipoxin A4. Herein, we report a total synthesis of the methyl ester of 15-oxo-LXA4 to be used in investigations of potential electrophilic bioactivity of this metabolite. The methyl ester of 15-oxo-LXA4 was synthesized in a convergent 15 step (9 steps longest linear) sequence starting from 1-octyn-3-ol and 2-deoxy-d-ribose with Sonogashira and Suzuki cross-couplings of a MIDA boronate as key steps. |
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| Keywords: | Eicosanoid Electrophile Palladium-catalyzed coupling MIDA boronate |
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