Syntheses of Showdomycin and its Anomer Using N-(Triisopropylsilyl)pyrrole as a Synthetic Equivalent for the Maleimide C3-Anion
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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.
Synthesis: journal of synthetic organic chemistry
Organic Chemical Synthesis