A New Facile Synthesis of D-4-Pterosin B and D-4-Bromopterosin, Deuterated Analogues of Ptaquiloside

Ptaquiloside (Pta) is a potent carcinogen present in bracken fern and in soilmatrices, that can potentially leach to the aquatic environment. More recently its presence inthe 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 massspectrometry. Pterosin sesquiterpenes are also involved in many patented biomedicalprotocols. In this work we introduce a new and convenient approach to the synthesis inthree 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.

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 d(4)-pterosin B (d(4)-Ptb) and d(4)-bromopterosin (d(4)-BrPt), useful as internal standards in the quantification of ptaquiloside. OI sindona, giovanni/0000-0002-5623-5795; Tagarelli, Antonio/0000-0002-8811-1631