Total synthesis of streptonigrin

FZ Basha, S Hibino, D Kim, WE Pye…

Index: 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

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Citation Number: 40

Abstract

formed into the chloride 16 (SOC12/benzene; mp 121-122" C) which was alkylated with N- cyanomethylpyrrolidine (MezSO, 43" C) to form quaternary salt 17. Without isolation, 17 was treated first with t-BuOK in THF/MezSO (2: l) at-12 OC (deoxygenated argon, 10 min) and then with oxalic acid in THF/H20 (2: l) at reflux to yield aldehyde 18: 7b.'3 35% from acetate 14; NMR (CDCI3) 6 2.1, 2.75 (3 H each, s), 5.05 (2 H, s), 9.5 (IH, s).