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Total synthesis of (±)-streptonigrin: de novo construction of a pentasubstituted pyridine using ring-closing metathesis

The synthesis of the potent antitumor agent (±)-streptonigrin has been achieved in 14 linear steps and 11% overall yield from ethyl glyoxalate. The synthesis features a challenging ring-closing metathesis reaction, followed by elimination and aromatization, to furnish a key pentasubstituted pyridine... Full description

Journal Title: Journal of the American Chemical Society 19 October 2011, Vol.133(41), pp.16418-21
Main Author: Donohoe, Timothy J
Other Authors: Jones, Christopher R , Barbosa, Luiz C A
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: E-ISSN: 1520-5126 ; PMID: 21942896 Version:1 ; DOI: 10.1021/ja207835w
Link: http://pubmed.gov/21942896
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recordid: medline21942896
title: Total synthesis of (±)-streptonigrin: de novo construction of a pentasubstituted pyridine using ring-closing metathesis
format: Article
creator:
  • Donohoe, Timothy J
  • Jones, Christopher R
  • Barbosa, Luiz C A
subjects:
  • Pyridines -- Chemistry
  • Streptonigrin -- Chemical Synthesis
ispartof: Journal of the American Chemical Society, 19 October 2011, Vol.133(41), pp.16418-21
description: The synthesis of the potent antitumor agent (±)-streptonigrin has been achieved in 14 linear steps and 11% overall yield from ethyl glyoxalate. The synthesis features a challenging ring-closing metathesis reaction, followed by elimination and aromatization, to furnish a key pentasubstituted pyridine fragment.
language: eng
source:
identifier: E-ISSN: 1520-5126 ; PMID: 21942896 Version:1 ; DOI: 10.1021/ja207835w
fulltext: fulltext
issn:
  • 15205126
  • 1520-5126
url: Link


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titleTotal synthesis of (±)-streptonigrin: de novo construction of a pentasubstituted pyridine using ring-closing metathesis
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descriptionThe synthesis of the potent antitumor agent (±)-streptonigrin has been achieved in 14 linear steps and 11% overall yield from ethyl glyoxalate. The synthesis features a challenging ring-closing metathesis reaction, followed by elimination and aromatization, to furnish a key pentasubstituted pyridine fragment.
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titleTotal synthesis of (±)-streptonigrin: de novo construction of a pentasubstituted pyridine using ring-closing metathesis
descriptionThe synthesis of the potent antitumor agent (±)-streptonigrin has been achieved in 14 linear steps and 11% overall yield from ethyl glyoxalate. The synthesis features a challenging ring-closing metathesis reaction, followed by elimination and aromatization, to furnish a key pentasubstituted pyridine fragment.
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abstractThe synthesis of the potent antitumor agent (±)-streptonigrin has been achieved in 14 linear steps and 11% overall yield from ethyl glyoxalate. The synthesis features a challenging ring-closing metathesis reaction, followed by elimination and aromatization, to furnish a key pentasubstituted pyridine fragment.
doi10.1021/ja207835w
pmid21942896
date2011-10-19