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

…, LJ Walport, MR Tatton, M O'Hagan…

文献索引：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. Journal of Organic Chemistry, 2013 , vol. 78, # 24 p. 12338 - 12350

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被引用次数: 17

摘要

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 ...