C-Nucleoside studies. Part 7. A new synthesis of showdomycin, 2-β-D-ribofuranosylmaleimide

J. Grant Buchanan; Alan R. Edgar; Michael J. Power; Colin T. Shanks

C-Nucleoside studies. Part 7. A new synthesis of showdomycin, 2-β-D-ribofuranosylmaleimide

J. Grant Buchanan, Alan R. Edgar, Michael J. Power, Colin T. Shanks

School of Engineering & Physical Sciences

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

17 Citations (Scopus)

Abstract

Showdomycin, 2-ß-D-ribofuranosylmaleimide (1), has been prepared in six stages from 2,3,5-tri-O-benzyl-ß-D-ribofuranosylethyne (2) in 23% overall yield (8% from D-ribose). Dimethoxycarbonylation of (2) afforded the substituted maleic ester (4) which was converted, in two stages, into the crystalline anhydride (10). Ammonolysis followed by ring-closure gave the crystalline maleimide (13), which was debenzylated with boron trichloride to give showdomycin.

Original language	English
Pages (from-to)	225-227
Number of pages	3
Journal	Journal of the Chemical Society, Perkin Transactions 1
Publication status	Published - 1979

Cite this

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title = "C-Nucleoside studies. Part 7. A new synthesis of showdomycin, 2-β-D-ribofuranosylmaleimide",

abstract = "Showdomycin, 2-{\ss}-D-ribofuranosylmaleimide (1), has been prepared in six stages from 2,3,5-tri-O-benzyl-{\ss}-D-ribofuranosylethyne (2) in 23\% overall yield (8\% from D-ribose). Dimethoxycarbonylation of (2) afforded the substituted maleic ester (4) which was converted, in two stages, into the crystalline anhydride (10). Ammonolysis followed by ring-closure gave the crystalline maleimide (13), which was debenzylated with boron trichloride to give showdomycin.",

author = "Buchanan, \{J. Grant\} and Edgar, \{Alan R.\} and Power, \{Michael J.\} and Shanks, \{Colin T.\}",

year = "1979",

language = "English",

pages = "225--227",

journal = "Journal of the Chemical Society, Perkin Transactions 1",

issn = "1472-7781",

publisher = "Chemical Society",

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TY - JOUR

T1 - C-Nucleoside studies. Part 7. A new synthesis of showdomycin, 2-β-D-ribofuranosylmaleimide

AU - Buchanan, J. Grant

AU - Edgar, Alan R.

AU - Power, Michael J.

AU - Shanks, Colin T.

PY - 1979

Y1 - 1979

N2 - Showdomycin, 2-ß-D-ribofuranosylmaleimide (1), has been prepared in six stages from 2,3,5-tri-O-benzyl-ß-D-ribofuranosylethyne (2) in 23% overall yield (8% from D-ribose). Dimethoxycarbonylation of (2) afforded the substituted maleic ester (4) which was converted, in two stages, into the crystalline anhydride (10). Ammonolysis followed by ring-closure gave the crystalline maleimide (13), which was debenzylated with boron trichloride to give showdomycin.

AB - Showdomycin, 2-ß-D-ribofuranosylmaleimide (1), has been prepared in six stages from 2,3,5-tri-O-benzyl-ß-D-ribofuranosylethyne (2) in 23% overall yield (8% from D-ribose). Dimethoxycarbonylation of (2) afforded the substituted maleic ester (4) which was converted, in two stages, into the crystalline anhydride (10). Ammonolysis followed by ring-closure gave the crystalline maleimide (13), which was debenzylated with boron trichloride to give showdomycin.

M3 - Article

SN - 1472-7781

SP - 225

EP - 227

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

ER -

C-Nucleoside studies. Part 7. A new synthesis of showdomycin, 2-β-D-ribofuranosylmaleimide

Abstract

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