In this note, we report the discovery of a novel pyridinium chlorochroamte-catalyzed process in which an -bromomethyl-tetrahydrofuran bond was oxidatively cleaved to give a gamma-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).
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 / Piccialli, Vincenzo. - In: MOLBANK. - ISSN 1422-8599. - 2017:4(2017), pp. M969-1-M969-5. [10.3390/M969]
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
Piccialli, Vincenzo
2017
Abstract
In this note, we report the discovery of a novel pyridinium chlorochroamte-catalyzed process in which an -bromomethyl-tetrahydrofuran bond was oxidatively cleaved to give a gamma-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).I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
