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…
Index: 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
Full Text: HTML
Citation Number: 17
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 ...
Related Articles:
[Yano, Tomotake; Kuroboshi, Manabu; Tanaka, Hideo Tetrahedron Letters, 2010 , vol. 51, # 4 p. 698 - 701]
[Kuroboshi, Manabu; Yano, Tomotake; Kamenoue, Shogo; Kawakubo, Hiromu; Tanaka, Hideo Tetrahedron, 2011 , vol. 67, # 32 p. 5825 - 5831]
[Kuroboshi, Manabu; Yano, Tomotake; Kamenoue, Shogo; Kawakubo, Hiromu; Tanaka, Hideo Tetrahedron, 2011 , vol. 67, # 32 p. 5825 - 5831]
[Yakhvarov; Budnikova; Tazeev; Sinyashin Russian Chemical Bulletin, 2002 , vol. 51, # 11 p. 2059 - 2064]
A novel imido-transfer reaction of aldehydes with Ph 3 P NTs using RuCl 2 (PPh 3) 3 as catalyst
[Jain, Suman L.; Sharma, Vishal B.; Sain, Bir Tetrahedron Letters, 2004 , vol. 45, # 22 p. 4341 - 4343]