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Deprotecting Dithiane-Containing Alkaloids

Fraser F. Fleming*, Lee Funk, Ramazan Altundas and Yong Tu

*Duquesne University, Department of Chemistry & Biochemistry, Pittsburgh, Pennsylvania 15282-1530, Email:

F. F. Fleming, L. Funk, R. Altundas, Y. Tu, J. Org. Chem., 2001, 66, 6502 - 6504.

DOI: 10.1021/jo0157829


Oxidative deprotection of several dithiane-containing alkaloids in the presence of bis(trifluoroacetoxy)iodobenzene and a nonchromatic purification cleanly generates the corresponding ketoamines. The described procedure is ideal for labile alkaloids.

see article for more examples

proposed mechanism (simplified)

Key Words

dithianes, bis(trifluoroacetoxy)iodobenzene

ID: J42-Y2001-450