Total synthesis of the antitumor antibiotic streptonigrin

SM Weinreb, FZ Basha, S Hibino…

Index: Weinreb,S.M.; Basha,F.Z.; Hibino,S. Journal of the American Chemical Society, 1982 , vol. 104, p. 536

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Citation Number: 61

Abstract

Abstract: Full details of the previously reported total synthesis of streptonigrin (1) are presented. The successful synthetic strategy outlined in Scheme I involves use of an imino Diels-Alder cycloaddition for construction of the pyridine C ring of 1 and a modified Friedlander synthesis for annulation of the AB quinoline quinone ring system.

~69%

Total synthesis of streptonigrin

[Basha, Fatima Z.; Hibino, Satoshi; Kim, Deukjoon; Pye, Walter E.; Wu, Tai-Teh; Weinreb, Steven M. Journal of the American Chemical Society, 1980 , vol. 102, # 11 p. 3962 - 3964]

Determination of the absolute configuration of the chiral bi...

[Tennant, Shaun; Rickards, Rodney W. Tetrahedron, 1997 , vol. 53, # 44 p. 15101 - 15114]