FORMAL SYNTHESIS OF LAURENCIONE <i>via</i> MgBr2–CATALYZED REARRANGEMENT OF α,β-EPOXYKETONES TO 1,2-DIKETONES
DOI:
https://doi.org/10.1007/355Keywords:
cyclopropanols, α, β-epoxyketones, oxidation, 1, 2-diketones, 2-hydroxytetrahydrofuran-3-onesAbstract
A flexible method for synthesis of laurencione, a marine natural product, and its benzyl and tert-butyl-methylsilyl-protected precursors was developed utilizing 3-hydroxypropionic acid ethyl ester as a starting material. The synthetic route consists of Kulinkovich cyclopropanation of a hydroxyl-protected ester, followed by oxidation of the resulting cyclopropanol to the appropriate oxiranyl ketone and its MgBr2·OEt2-catalyzed rearrangement to 1,2‑diketone.
Also published in Chemistry of Heterocyclic Compounds, 2013, 49 (5), pp 676-682