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Synthesis of an Electrophilic Keto-Tetraene 15-oxo-Lipoxin A4 Methyl Ester via a MIDA Boronate.

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.

SUBMITTER: Woodcock SR

PROVIDER: S-EPMC6677397 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature

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Synthesis of an Electrophilic Keto-Tetraene 15-oxo-Lipoxin A4 Methyl Ester via a MIDA Boronate.

Woodcock Steven R SR Wendell Stacy G SG Schopfer Francisco J FJ Freeman Bruce A BA

Tetrahedron letters 20180810 39

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 S ...[more]

PMID: 31379396

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