K. Lood, B. Schmidt
Stereoselective Synthesis of Conjugated Polyenes Based on Tethered Olefin Metathesis and Carbonyl Olefination: Application to the Total Synthesis of (+)-Bretonin B
J. Org. Chem. 2020, 85, 5122-5130
DOI: 10.1021/acs.joc.0c00446
We report the total synthesis of enantiomerically pure (+)-bretonin B, a marine natural product that was first isolated from a sponge collected off the coast of Brittany. The structure comprises a synthetically challenging E,Z,E-triene pattern that was accessed using an unconventional tethered olefin metathesis reaction in combination with a Julia-Kocienski-olefination.
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