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).

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methyl 5-amino-6-(7-amino-6-methoxy-5,8-dioxo-5,8-dihydroquinolin-2-yl)-4-(2-(benzyloxy)-3,4-dimethoxyphenyl)-3-methylpicolinate Structure

74615-13-7

methyl 5-amino-...

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STREPTONIGRIN METHYL ESTER Structure

3398-48-9

STREPTONIGRIN M...

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74615-12-6

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STREPTONIGRIN METHYL ESTER Structure

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STREPTONIGRIN METHYL ESTER Structure

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74614-86-1

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STREPTONIGRIN METHYL ESTER Structure

3398-48-9

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1-(1-ethyliddine-2-butenyl)-3,4-dimethoxy-2-(phenylmethoxy)benzene Structure

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STREPTONIGRIN METHYL ESTER Structure

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β-ethenyl-3,4-dimethoxy-2-(phenylmethoxy)benzeneethanol Structure

74614-85-0

β-ethenyl-3,4-d...

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STREPTONIGRIN METHYL ESTER Structure

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methyl 4-(2-(benzyloxy)-3,4-dimethoxyphenyl)-3,6-dimethylpicolinate Structure

74614-95-2

methyl 4-(2-(be...

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STREPTONIGRIN METHYL ESTER Structure

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74615-01-3

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STREPTONIGRIN METHYL ESTER Structure

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methyl 5-amino-4-(3,4-dimethoxy-2-(phenylmethoxy)phenyl)-6-formyl-3-methyl-2-pyridinecarboxylate Structure

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STREPTONIGRIN METHYL ESTER Structure

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methyl 6-(chloromethyl)-4-(3,4-dimethoxy-2-(phenylmethoxy)phenyl)-3-methyl-2-pyridinecarboxylate Structure

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STREPTONIGRIN METHYL ESTER Structure

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4-(2-(benzyloxy)-3,4-dimethoxyphenyl)-2-(methoxycarbonyl)-3,6-dimethylpyridine 1-oxide Structure

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methyl 5-amino-4-[3,4-dimethoxy-2-(phenylmethoxy)phenyl]-6-(hydroxymethyl)-3-methyl-2-pyridinecarboxylate Structure

74615-05-7

methyl 5-amino-...

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STREPTONIGRIN METHYL ESTER Structure

3398-48-9

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74615-02-4

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STREPTONIGRIN METHYL ESTER Structure

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methyl 5-amino-4[3,4-dimethoxy-2-(phenylmethoxy)phenyl]-6-[3-[6-methoxy-5-[(phenylsulfonyl)oxy]phenyl]-2-quinolyl]-3-methyl-2-pyridinecarboxylate Structure

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STREPTONIGRIN METHYL ESTER Structure

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methyl 6-[(acetyloxy)methyl]-4-[3,4-dimethoxy-2-(phenylmethoxy)phenyl]-3-methyl-2-pyridinecarboxylate Structure

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methyl 5-amino-(3,4-dimethoxy-2-(phenylmethoxy)phenyl)-6-(2-(dimethoxyphosphinyl)acetyl)-3-methyl-2-pyridinecarboxylate Structure

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methyl 5-amino-[3,4-dimethoxy-2-(phenylmethoxy)phenyl]-6-[2-(dimethoxyphosphinyl)-1-hydroxyethyl]-3-methyl-2-pyridinecarboxylate Structure

79953-20-1

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STREPTONIGRIN METHYL ESTER Structure

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methyl 5-amino-4[3,4-dimethoxy-2-(phenylmethoxy)phenyl]-6-(5-hydroxy-6-methoxy-2-quinolyl)-3-methyl-2-pyridinecarboxylate Structure

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STREPTONIGRIN METHYL ESTER Structure

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STREPTONIGRIN METHYL ESTER Structure

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methyl (E)-5-amino-4-(2-(benzyloxy)-3,4-dimethoxyphenyl)-6-(3-(3-methoxy-6-nitro-2-((phenylsulfonyl)oxy)phenyl)acryloyl)-3-methylpicolinate Structure

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STREPTONIGRIN METHYL ESTER Structure

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