Journal article
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
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Bibliographic Details
- 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
Item Description
- Language:
- English
- Keywords:
Terms of use
- Copyright date:
- 2013
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