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Open AccessCommunication
Molbank 2017, 2017(4), M969; doi: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

Department of Chemical Sciences, University of Naples “Federico II”, Complesso di Monte S. Angelo, Via Cintia 4, 80126 Naples, Italy
Received: 1 December 2017 / Revised: 8 December 2017 / Accepted: 11 December 2017 / Published: 13 December 2017
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [881 KB, uploaded 13 December 2017]   |  

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 1H-NMR, 13C-NMR, FTIR (Fourier transform infrared), EIMS (Electron impact mass spectrometry) and HRESIMS (High-resolution electrospray ionisation mass spectrometry). View Full-Text
Keywords: pyridinium chlorochromate; α-bromomethyl-tetrahydrofuran; oxidative cleavage; γ-lactone pyridinium chlorochromate; α-bromomethyl-tetrahydrofuran; oxidative cleavage; γ-lactone
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Piccialli, V. 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. Molbank 2017, 2017, M969.

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