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Synthesis 2003(12): 1837-1843
DOI: 10.1055/s-2003-41026
DOI: 10.1055/s-2003-41026
PAPER
© Georg ThiemeVerlag Stuttgart · New York
Syntheses of Showdomycin andits Anomer Using N-(Triisopropylsilyl)pyrrole asa Synthetic Equivalent for the Maleimide C3-Anion
Further Information
Received
9 July 2003
Publication Date:
13 August 2003 (online)
Publication History
Publication Date:
13 August 2003 (online)
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Abstract
Showdomycin (1) and its anomer (2) have been prepared in four steps fromreadily available trichloroacetimidate 9.The key step involves reaction of the last compound with the titlepyrrole 3 so as to form a chromatographically separable mixtureof the pyrrole C-glycosides 10 and 11. Thesepyrroles are desilylated then oxidized to the corresponding maleimidesusing PCC.
Key words
nucleosides - pyrroles - trichloroacetimidates - C-glycosides - maleimides - oxidation
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References
Compound 7 canbe purchased from the Aldrich Chemical Company.