A Novel PCC-Catalyzed Process Involving the Oxidative Cleavage of an α-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

Abstract

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 1 H-NMR, 13 C-NMR, FTIR (Fourier transform infrared), EIMS (Electron impact mass spectrometry) and HRESIMS (High-resolution electrospray ionisation mass spectrometry).

Antiproliferative Activity of Mycalin A and Its Analogues on Human Skin Melanoma and Human Cervical Cancer Cells

“…Lastly, lactone 11 was prepared by using a PCC (pyridinium chlorochromate)-catalyzed process (PCC/H 5 IO 6 system) recently discovered in our laboratory [ 16 ], starting from mycalin A acetate ( Scheme 5 ). Okamura et al [ 17 ] have postulated that the actual oxidizing agent, under the above conditions, is chlorochromateperiodate (CCP), an oxidizing species more powerful than PCC, derived from the condensation of PCC and H 5 IO 6 with the elimination of water.…”