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

Abstract:
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.
Publication status:
Published

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Publisher copy:
10.1021/ja207835w

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Journal:
Journal of the American Chemical Society More from this journal
Volume:
133
Issue:
41
Pages:
16418-16421
Publication date:
2011-10-01
DOI:
EISSN:
1520-5126
ISSN:
0002-7863
Language:
English
Keywords:
Pubs id:
pubs:180442
UUID:
uuid:a8c1c0da-8835-429b-a19b-83792e88b376
Local pid:
pubs:180442
Source identifiers:
180442
Deposit date:
2012-12-19

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