A Novel PCC-Catalyzed Process Involving the Oxidative Cleavage of an -Bromomethyl-tetrahydrofuran Bond. Synthesis of (2S,3R)-2-{(R)-Bromo[(2R,3R,5S,6R)-3,5-dibromo-6-ethyltetrahydro-2H-pyran-2-yl]methyl}-5-oxotetrahydrofuran-3-yl Benzoate

In this note, we report the discovery of a novel pyridinium chlorochroamte-catalyzed process in which an α-bromomethyl-tetrahydrofuran bond was oxidatively cleaved to give a γ-lactone functionality. The title compound was synthesized from a C15 polybrominated acetogenin compound, isolated from the marine sponge Mycale rotalis, by benzoylation followed by pyridinium chlorochromate-catalyzed oxidation. This new degraded derivative was fully characterized by 1H-NMR, 13C-NMR, FTIR (Fourier transform infrared), EIMS (Electron impact mass spectrometry) and HRESIMS (High-resolution electrospray ionisation mass spectrometry).