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: flemingf
duq.edu
F. F. Fleming, L. Funk, R. Altundas, Y. Tu, J. Org. Chem., 2001, 66, 6502 - 6504.
DOI: 10.1021/jo0157829
Abstract
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
