Syntheses of Showdomycin and its Anomer Using N-(Triisopropylsilyl)pyrrole as a Synthetic Equivalent for the Maleimide C3-Anion
Author(s)
L. Hungerford, Natasha
J. Armitt, David
G. Banwell, Martin
Griffith University Author(s)
Year published
2004
Metadata
Show full item recordAbstract
Showdomycin (1) and its anomer (2) have been prepared in four steps from readily available trichloroacetimidate 9.The key step involves reaction of the last compound with the title pyrrole 3 so as to form a chromatographically separable mixture of the pyrrole C-glycosides 10 and 11. Thesepyrroles are desilylated then oxidized to the corresponding maleimides using PCC.Showdomycin (1) and its anomer (2) have been prepared in four steps from readily available trichloroacetimidate 9.The key step involves reaction of the last compound with the title pyrrole 3 so as to form a chromatographically separable mixture of the pyrrole C-glycosides 10 and 11. Thesepyrroles are desilylated then oxidized to the corresponding maleimides using PCC.
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Journal Title
Synthesis: journal of synthetic organic chemistry
Volume
2003
Issue
12
Subject
Organic Chemical Synthesis
Analytical Chemistry
Organic Chemistry