Total Synthesis of the Antitumor Antibiotic (±)-Streptonigrin: First- and Second-Generation Routes for de Novo Pyridine Formation Using Ring-Closing Metathesis

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 di...

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Veröffentlicht in:	Journal of organic chemistry 2013-12, Vol.78 (24), p.12338-12350
Hauptverfasser:	Donohoe, Timothy J, Jones, Christopher R, Kornahrens, Anne F, Barbosa, Luiz C. A, Walport, Louise J, Tatton, Matthew R, O’Hagan, Michael, Rathi, Akshat H, Baker, David B
Format:	Artikel
Sprache:	eng
Schlagworte:	Antibiotics, Antineoplastic - chemical synthesis Antibiotics, Antineoplastic - chemistry Cyclization Molecular Structure Stereoisomerism Streptonigrin - chemical synthesis Streptonigrin - chemistry
Online-Zugang:	Volltext
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