Synthesis of the indole nucleoside antibiotics neosidomycin and SF-2140

J. Grant Buchanan, Jane Stoddart, Richard H. Wightman

Research output: Contribution to journalArticle

Abstract

The indole nucleoside antibiotics neosidomycin 5 and SF-2140 3 have been synthesized. Methyl 4-deoxy-2,3-O-isopropylidene-a-D-lyxo-hexopyranoside 8 was converted into methyl 1-chloro-1,4-dideoxy-2.3-di-O-pivaloyl-a-D- lyxo-hexopyranuronate 33 in five steps. Silver (I)-catalysed coupling of compound 33 with 3-(cyanomethyl)indole 20 gave stereoselectively an a-nucleoside which was converted into methyl 1-[3-(carbamoylmethyl)indol- 1-yl]-1,4-dideoxy-a-D-lyxo-hexopyranuronate (neosidomycin, 5). Coupling of compound 33 to 3-cyanomethyl-4-methoxyindole 23 by the sodium salt procedure, and subsequent deacylation, gave methyl 1-(3-cyanomethyl-4-methoxyindol-1-yl)-1, 4-dideoxy-a-D-lyxo-hexopyranuronate (SF-2140, 3). Neosidomycin, SF-2140, and their O-acyl derivatives adopt a conformation which differs from that of 1-(6-O-benzoyl-4-deoxy-2,3-O-pivaloyl-a-D-lyxo-hexopyranosyl) -3-(cyanomethyl)indole 29, in which the methyl uronate grouping of the antibiotics is present at a lower oxidation level.

Original languageEnglish
Pages (from-to)1417-1426
Number of pages10
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number11
Publication statusPublished - 1994

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Nucleosides
Anti-Bacterial Agents
Silver
Conformations
Salts
Sodium
Derivatives
Oxidation
indole
neosidomycin
SF 2140

Cite this

Buchanan, J. Grant ; Stoddart, Jane ; Wightman, Richard H. / Synthesis of the indole nucleoside antibiotics neosidomycin and SF-2140. In: Journal of the Chemical Society, Perkin Transactions 1. 1994 ; No. 11. pp. 1417-1426.
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abstract = "The indole nucleoside antibiotics neosidomycin 5 and SF-2140 3 have been synthesized. Methyl 4-deoxy-2,3-O-isopropylidene-a-D-lyxo-hexopyranoside 8 was converted into methyl 1-chloro-1,4-dideoxy-2.3-di-O-pivaloyl-a-D- lyxo-hexopyranuronate 33 in five steps. Silver (I)-catalysed coupling of compound 33 with 3-(cyanomethyl)indole 20 gave stereoselectively an a-nucleoside which was converted into methyl 1-[3-(carbamoylmethyl)indol- 1-yl]-1,4-dideoxy-a-D-lyxo-hexopyranuronate (neosidomycin, 5). Coupling of compound 33 to 3-cyanomethyl-4-methoxyindole 23 by the sodium salt procedure, and subsequent deacylation, gave methyl 1-(3-cyanomethyl-4-methoxyindol-1-yl)-1, 4-dideoxy-a-D-lyxo-hexopyranuronate (SF-2140, 3). Neosidomycin, SF-2140, and their O-acyl derivatives adopt a conformation which differs from that of 1-(6-O-benzoyl-4-deoxy-2,3-O-pivaloyl-a-D-lyxo-hexopyranosyl) -3-(cyanomethyl)indole 29, in which the methyl uronate grouping of the antibiotics is present at a lower oxidation level.",
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Synthesis of the indole nucleoside antibiotics neosidomycin and SF-2140. / Buchanan, J. Grant; Stoddart, Jane; Wightman, Richard H.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 11, 1994, p. 1417-1426.

Research output: Contribution to journalArticle

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