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Synthesis of an Electrophilic Keto-Tetraene 15-oxo-Lipoxin A4 Methyl Ester via a MIDA Boronate.
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ABSTRACT:
SUBMITTER: Woodcock SR
PROVIDER: S-EPMC6677397 | biostudies-literature | 2018 Sep
REPOSITORIES: biostudies-literature
Publications
Synthesis of an Electrophilic Keto-Tetraene 15-oxo-Lipoxin A<sub>4</sub> Methyl Ester <i>via</i> a MIDA Boronate.
Tetrahedron letters 20180810 39
15-oxo-Lipoxin A<sub>4</sub> (15-oxo- LXA<sub>4</sub>) has been identified as a natural metabolite of the fatty acid signaling mediator Lipoxin A<sub>4</sub>. Herein, we report a total synthesis of the methyl ester of 15-oxo-LXA<sub>4</sub> to be used in investigations of potential electrophilic bioactivity of this metabolite. The methyl ester of 15-oxo-LXA<sub>4</sub> was synthesized in a convergent 15 step (9 steps longest linear) sequence starting from 1-octyn-3-ol and 2-deoxy-D-ribose with S ...[more]