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

doi:10.3390/molecules17055795

This article is

freely available
re-usable

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

Article

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

Mohamed Attya* , Monica Nardi, Antonio Tagarelli and Giovanni Sindona

Department of Chemistry, University of Calabria, 87036 Arcavacata di Rende (Cosenza), Italy

* Author to whom correspondence should be addressed.

Received: 26 April 2012; in revised form: 9 May 2012 / Accepted: 14 May 2012 / Published: 16 May 2012

(This article belongs to the Special Issue Challenges in Synthetic Chemistry)

Download PDF Full-Text [218 KB, uploaded 16 May 2012 08:57 CEST]

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

Article Statistics

Click here to load and display the download statistics.

Cite This Article

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.

AMA 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(5):5795-5802.

Chicago/Turabian Style

Attya, Mohamed; Nardi, Monica; Tagarelli, Antonio; Sindona, Giovanni. 2012. "A New Facile Synthesis of D₄-Pterosin B and D₄-Bromopterosin, Deuterated Analogues of Ptaquiloside." Molecules 17, no. 5: 5795-5802.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert