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Molecules 2012, 17(5), 5795-5802; doi:10.3390/molecules17055795

A New Facile Synthesis of D4-Pterosin B and D4-Bromopterosin, Deuterated Analogues of Ptaquiloside

Department of Chemistry, University of Calabria, 87036 Arcavacata di Rende (Cosenza), Italy
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Received: 26 April 2012 / Revised: 9 May 2012 / Accepted: 14 May 2012 / Published: 16 May 2012
(This article belongs to the Special Issue Challenges in Synthetic Chemistry)
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Abstract

Ptaquiloside (Pta) is a potent carcinogen present in bracken fern and in soil matrices, that can potentially leach to the aquatic environment. More recently its presence in the milk of different farm animals has been reported. Pterosin B (Ptb) and bromopterosin (BrPt) represent the most convenient analogues in the detection of ptaquiloside by mass spectrometry. Pterosin sesquiterpenes are also involved in many patented biomedical protocols. In this work we introduce a new and convenient approach to the synthesis in three steps and more than 80% yield of d4-pterosin B (d4-Ptb) and d4-bromopterosin (d4-BrPt), useful as internal standards in the quantification of ptaquiloside.
Keywords: natural products; total synthesis; isotopic labelling; ptaquiloside; pterosin B; d4-pterosin; d4-bromopterosin natural products; total synthesis; isotopic labelling; ptaquiloside; pterosin B; d4-pterosin; d4-bromopterosin
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Attya, M.; Nardi, M.; Tagarelli, A.; Sindona, G. A New Facile Synthesis of D4-Pterosin B and D4-Bromopterosin, Deuterated Analogues of Ptaquiloside. Molecules 2012, 17, 5795-5802.

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