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Total synthesis of the antitumor antibiotic (±)-streptonigrin: first- and second-generation routes for de novo pyridine formation using ring-closing metathesis.

Abstract:

The total synthesis of (±)-streptonigrin, a potent tetracyclic aminoquinoline-5,8-dione antitumor antibiotic that reached phase II clinical trials in the 1970s, is described. Two routes to construct a key pentasubstituted pyridine fragment are depicted, both relying on ring-closing metathesis but differing in the substitution and complexity of the precursor to cyclization. Both routes are short and high yielding, with the second-generation approach ultimately furnishing (±)-streptonigrin in 1...

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Publication status:
Published

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Publisher copy:
10.1021/jo402388f

Authors


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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Kornahrens, AF More by this author
Barbosa, LC More by this author
Walport, LJ More by this author
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Journal:
The Journal of organic chemistry
Volume:
78
Issue:
24
Pages:
12338-12350
Publication date:
2013-12-12
DOI:
EISSN:
1520-6904
ISSN:
0022-3263
URN:
uuid:1e2437ca-498e-4820-87c7-e7caf712dd4f
Source identifiers:
444040
Local pid:
pubs:444040

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