Syntheses of showdomycin and its anomer using N-(triisopropylsilyl)pyrrole as a synthetic equivalent for the maleimide C3-anion

Natasha L. Hungerford; David J. Armitt; Martin G. Banwell

doi:10.1055/s-2003-41026

Syntheses of showdomycin and its anomer using N-(triisopropylsilyl)pyrrole as a synthetic equivalent for the maleimide C3-anion

Natasha L. Hungerford, David J. Armitt, Martin G. Banwell^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

16 Citations (Scopus)

Abstract

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. These pyrroles are desilylated then oxidized to the corresponding maleimides using PCC.

Original language	English
Pages (from-to)	1837-1843
Number of pages	7
Journal	Synthesis
Issue number	12
DOIs	https://doi.org/10.1055/s-2003-41026
Publication status	Published - 2003

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title = "Syntheses of showdomycin and its anomer using N-(triisopropylsilyl)pyrrole as a synthetic equivalent for the maleimide C3-anion",

abstract = "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. These pyrroles are desilylated then oxidized to the corresponding maleimides using PCC.",

keywords = "C-glycosides, Maleimides, Nucleosides, Oxidation, Pyrroles, Trichloroacetimidates",

author = "Hungerford, {Natasha L.} and Armitt, {David J.} and Banwell, {Martin G.}",

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AU - Hungerford, Natasha L.

AU - Armitt, David J.

AU - Banwell, Martin G.

PY - 2003

Y1 - 2003

N2 - 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. These pyrroles are desilylated then oxidized to the corresponding maleimides using PCC.

AB - 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. These pyrroles are desilylated then oxidized to the corresponding maleimides using PCC.

KW - C-glycosides

KW - Maleimides

KW - Nucleosides

KW - Oxidation

KW - Pyrroles

KW - Trichloroacetimidates

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U2 - 10.1055/s-2003-41026

DO - 10.1055/s-2003-41026

M3 - Article

SN - 0039-7881

SP - 1837

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JO - Synthesis

JF - Synthesis

IS - 12

ER -

Syntheses of showdomycin and its anomer using N-(triisopropylsilyl)pyrrole as a synthetic equivalent for the maleimide C3-anion

Abstract

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