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Tetrahedron letters

Total syntheses of (+)-nogarene and (+)-7, 8-dihydronogarene

M Kawasaki, F Matsuda, S Terashima

文献索引：Kawasaki, Motoji; Matsuda, Fuyuhiko; Terashima, Shiro Tetrahedron Letters, 1986 , vol. 27, # 19 p. 2145 - 2148

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被引用次数: 24

摘要

Download full text in PDF Opens in a new window. Article suggestions will be shown in a dialog on return to ScienceDirect. ... Please enable JavaScript to use all the features on this page. ... Total syntheses of the title compounds, the simplest and the hitherto unknown novel nogalamycin congeners, were first accomplished by elaborating the CDEF-ring system ( ) from the methyl ketone ( ) and subjecting to regioselective Diels-Alder reaction with the bistrimethylsilyl ...

(2R,3R,4S,5S)-(-)-6-(tert-butyldimethylsilyloxy)-4-(N-methoxycarbonyl-N-methylamino)-3,5-bis(methoxymethyloxy)-2-(1,4,5,8-tetramethoxy-2-naphthalenyl)-2-hexanol结构式

(2R,3R,4S,5S)-(...

~%

(2R,3S,4R,5R,6R)-(+)-3,5-diacetoxy-4-dimethylamino-8-hydroxy-6-methyl-2,6-epoxy-3,4,5,6-tetrahydro-2H-naphthaleno[1,2-b]oxocine-9,12-dione结构式

(2R,3S,4R,5R,6R...

(2S,3S,4R,5R)-(-)-3-(N-methoxycarbonyl-N-methylamino)-2,4-bis(methoxymethyloxy)-5-(1,4,5,8-tetramethoxy-2-naphthalenyl)-1,5-hexanediol结构式

(2S,3S,4R,5R)-(...

~%

(2R,3S,4R,5R,6R)-(+)-3,5-diacetoxy-4-dimethylamino-8-hydroxy-6-methyl-2,6-epoxy-3,4,5,6-tetrahydro-2H-naphthaleno[1,2-b]oxocine-9,12-dione结构式

(2R,3S,4R,5R,6R...

(3S,4R,5R,6R)-4-(N-methoxycarbonyl-N-methylamino)-3,5-bis(methoxymethyloxy)-6-methyl-6-(1,4,5,8-tetramethoxy-2-naphthalenyl)tetrahydro-2-pyranone结构式

(3S,4R,5R,6R)-4...

~%

(2R,3S,4R,5R,6R)-(+)-3,5-diacetoxy-4-dimethylamino-8-hydroxy-6-methyl-2,6-epoxy-3,4,5,6-tetrahydro-2H-naphthaleno[1,2-b]oxocine-9,12-dione结构式

(2R,3S,4R,5R,6R...

(2R,3R,4R,5S,6R)-(-)-4-(N-methoxycarbonyl-N-methylamino)-3,5,6-tris(methoxymethyloxy)-2-methyl-2-(1,4,5,8-tetramethoxy-2-naphthalenyl)tetrahydropyran结构式

(2R,3R,4R,5S,6R...

~%

(2R,3S,4R,5R,6R)-(+)-3,5-diacetoxy-4-dimethylamino-8-hydroxy-6-methyl-2,6-epoxy-3,4,5,6-tetrahydro-2H-naphthaleno[1,2-b]oxocine-9,12-dione结构式

(2R,3S,4R,5R,6R...

(2R,3S,4R,5R,6R)-4-(dimethylamino)-9,12-dimethoxy-6-methyl-3,4,5,6-tetrahydro-2H-2,6-epoxynaphtho[1,2-b]oxocine-3,5,8-triol结构式

(2R,3S,4R,5R,6R...

~%

(2R,3S,4R,5R,6R)-(+)-3,5-diacetoxy-4-dimethylamino-8-hydroxy-6-methyl-2,6-epoxy-3,4,5,6-tetrahydro-2H-naphthaleno[1,2-b]oxocine-9,12-dione结构式

(2R,3S,4R,5R,6R...

(2R,3R,4R,5S,6R)-(+)-2-(5,8-dimethoxy-1,4-dioxo-2-naphthalenyl)-4-dimethylamino-3,5,6-tris(methoxymethyloxy)-2-methyltetrahydropyran结构式

(2R,3R,4R,5S,6R...

~%

(2R,3S,4R,5R,6R)-(+)-3,5-diacetoxy-4-dimethylamino-8-hydroxy-6-methyl-2,6-epoxy-3,4,5,6-tetrahydro-2H-naphthaleno[1,2-b]oxocine-9,12-dione结构式

(2R,3S,4R,5R,6R...

2-((2R,3R,4R,5S,6R)-4-(dimethylamino)-3,5,6-tris(methoxymethoxy)-2-methyltetrahydro-2H-pyran-2-yl)-5,8-dimethoxynaphthalene-1,4-diol结构式

2-((2R,3R,4R,5S...

~%

(2R,3S,4R,5R,6R)-(+)-3,5-diacetoxy-4-dimethylamino-8-hydroxy-6-methyl-2,6-epoxy-3,4,5,6-tetrahydro-2H-naphthaleno[1,2-b]oxocine-9,12-dione结构式

(2R,3S,4R,5R,6R...

(2R,3R,4S,5S)-(-)-6-(tert-butyldimethylsilyloxy)-4-(N-methoxycarbonyl-N-methylamino)-3,5-bis(methoxymethyloxy)-2-(1,4,5,8-tetramethoxy-2-naphthalenyl)-2-hexanol结构式

(2R,3R,4S,5S)-(...

~%

(2R,3S,4R,5R,6R)-(+)-3,5-diacetoxy-9,12-dimethoxy-4-dimethylamino-8-hydroxy-6-methyl-2,6-epoxy-3,4,5,6-tetrahydro-2H-naphthaleno[1,2-b]oxocine结构式

(2R,3S,4R,5R,6R...

(2S,3S,4R,5R)-(-)-3-(N-methoxycarbonyl-N-methylamino)-2,4-bis(methoxymethyloxy)-5-(1,4,5,8-tetramethoxy-2-naphthalenyl)-1,5-hexanediol结构式

(2S,3S,4R,5R)-(...

~%

(2R,3S,4R,5R,6R)-(+)-3,5-diacetoxy-9,12-dimethoxy-4-dimethylamino-8-hydroxy-6-methyl-2,6-epoxy-3,4,5,6-tetrahydro-2H-naphthaleno[1,2-b]oxocine结构式

(2R,3S,4R,5R,6R...

(3S,4R,5R,6R)-4-(N-methoxycarbonyl-N-methylamino)-3,5-bis(methoxymethyloxy)-6-methyl-6-(1,4,5,8-tetramethoxy-2-naphthalenyl)tetrahydro-2-pyranone结构式

(3S,4R,5R,6R)-4...

~%

(2R,3S,4R,5R,6R)-(+)-3,5-diacetoxy-9,12-dimethoxy-4-dimethylamino-8-hydroxy-6-methyl-2,6-epoxy-3,4,5,6-tetrahydro-2H-naphthaleno[1,2-b]oxocine结构式

(2R,3S,4R,5R,6R...

(2R,3R,4R,5S,6R)-(-)-4-(N-methoxycarbonyl-N-methylamino)-3,5,6-tris(methoxymethyloxy)-2-methyl-2-(1,4,5,8-tetramethoxy-2-naphthalenyl)tetrahydropyran结构式

(2R,3R,4R,5S,6R...

~%

(2R,3S,4R,5R,6R)-(+)-3,5-diacetoxy-9,12-dimethoxy-4-dimethylamino-8-hydroxy-6-methyl-2,6-epoxy-3,4,5,6-tetrahydro-2H-naphthaleno[1,2-b]oxocine结构式

(2R,3S,4R,5R,6R...

(2R,3R,4R,5S,6R)-(+)-2-(5,8-dimethoxy-1,4-dioxo-2-naphthalenyl)-4-dimethylamino-3,5,6-tris(methoxymethyloxy)-2-methyltetrahydropyran结构式

(2R,3R,4R,5S,6R...

~%

(2R,3S,4R,5R,6R)-(+)-3,5-diacetoxy-9,12-dimethoxy-4-dimethylamino-8-hydroxy-6-methyl-2,6-epoxy-3,4,5,6-tetrahydro-2H-naphthaleno[1,2-b]oxocine结构式

(2R,3S,4R,5R,6R...

2-((2R,3R,4R,5S,6R)-4-(dimethylamino)-3,5,6-tris(methoxymethoxy)-2-methyltetrahydro-2H-pyran-2-yl)-5,8-dimethoxynaphthalene-1,4-diol结构式

2-((2R,3R,4R,5S...

~%

(2R,3S,4R,5R,6R)-(+)-3,5-diacetoxy-9,12-dimethoxy-4-dimethylamino-8-hydroxy-6-methyl-2,6-epoxy-3,4,5,6-tetrahydro-2H-naphthaleno[1,2-b]oxocine结构式

(2R,3S,4R,5R,6R...

(2R,3R,4R,5S,6R)-(-)-4-dimethylamino-3,5,6-tris(methoxymethyloxy)-2-methyl-2-(1,4,5,8-tetramethoxy-2-naphthalenyl)tetrahydropyran结构式

(2R,3R,4R,5S,6R...

~%

(2R,3S,4R,5R,6R)-(+)-3,5-diacetoxy-9,12-dimethoxy-4-dimethylamino-8-hydroxy-6-methyl-2,6-epoxy-3,4,5,6-tetrahydro-2H-naphthaleno[1,2-b]oxocine结构式

(2R,3S,4R,5R,6R...

(2R,3R,4S,5S)-(-)-6-(tert-butyldimethylsilyloxy)-4-(N-methoxycarbonyl-N-methylamino)-3,5-bis(methoxymethyloxy)-2-(1,4,5,8-tetramethoxy-2-naphthalenyl)-2-hexanol结构式

(2R,3R,4S,5S)-(...

~%

(2R,3R,4R,5S,6R)-(-)-4-(N-methoxycarbonyl-N-methylamino)-3,5,6-tris(methoxymethyloxy)-2-methyl-2-(1,4,5,8-tetramethoxy-2-naphthalenyl)tetrahydropyran结构式

(2R,3R,4R,5S,6R...

(2S,3S,4R,5R)-(-)-3-(N-methoxycarbonyl-N-methylamino)-2,4-bis(methoxymethyloxy)-5-(1,4,5,8-tetramethoxy-2-naphthalenyl)-1,5-hexanediol结构式

(2S,3S,4R,5R)-(...

~%

(2R,3R,4R,5S,6R)-(-)-4-(N-methoxycarbonyl-N-methylamino)-3,5,6-tris(methoxymethyloxy)-2-methyl-2-(1,4,5,8-tetramethoxy-2-naphthalenyl)tetrahydropyran结构式

(2R,3R,4R,5S,6R...

(3S,4R,5R,6R)-4-(N-methoxycarbonyl-N-methylamino)-3,5-bis(methoxymethyloxy)-6-methyl-6-(1,4,5,8-tetramethoxy-2-naphthalenyl)tetrahydro-2-pyranone结构式

(3S,4R,5R,6R)-4...

~%

(2R,3R,4R,5S,6R)-(-)-4-(N-methoxycarbonyl-N-methylamino)-3,5,6-tris(methoxymethyloxy)-2-methyl-2-(1,4,5,8-tetramethoxy-2-naphthalenyl)tetrahydropyran结构式

(2R,3R,4R,5S,6R...

(2S,3S,4R,5R)-(-)-3-(N-methoxycarbonyl-N-methylamino)-2,4-bis(methoxymethyloxy)-5-(1,4,5,8-tetramethoxy-2-naphthalenyl)-1,5-hexanediol结构式

(2S,3S,4R,5R)-(...

~%

2-((2R,3R,4R,5S,6R)-4-(dimethylamino)-3,5,6-tris(methoxymethoxy)-2-methyltetrahydro-2H-pyran-2-yl)-5,8-dimethoxynaphthalene-1,4-diol结构式

2-((2R,3R,4R,5S...

(3S,4R,5R,6R)-4-(N-methoxycarbonyl-N-methylamino)-3,5-bis(methoxymethyloxy)-6-methyl-6-(1,4,5,8-tetramethoxy-2-naphthalenyl)tetrahydro-2-pyranone结构式

(3S,4R,5R,6R)-4...

~%

2-((2R,3R,4R,5S,6R)-4-(dimethylamino)-3,5,6-tris(methoxymethoxy)-2-methyltetrahydro-2H-pyran-2-yl)-5,8-dimethoxynaphthalene-1,4-diol结构式

2-((2R,3R,4R,5S...

(2R,3R,4R,5S,6R)-(-)-4-(N-methoxycarbonyl-N-methylamino)-3,5,6-tris(methoxymethyloxy)-2-methyl-2-(1,4,5,8-tetramethoxy-2-naphthalenyl)tetrahydropyran结构式

(2R,3R,4R,5S,6R...

~%

2-((2R,3R,4R,5S,6R)-4-(dimethylamino)-3,5,6-tris(methoxymethoxy)-2-methyltetrahydro-2H-pyran-2-yl)-5,8-dimethoxynaphthalene-1,4-diol结构式

2-((2R,3R,4R,5S...

(2R,3R,4R,5S,6R)-(-)-4-dimethylamino-3,5,6-tris(methoxymethyloxy)-2-methyl-2-(1,4,5,8-tetramethoxy-2-naphthalenyl)tetrahydropyran结构式

(2R,3R,4R,5S,6R...

~%

2-((2R,3R,4R,5S,6R)-4-(dimethylamino)-3,5,6-tris(methoxymethoxy)-2-methyltetrahydro-2H-pyran-2-yl)-5,8-dimethoxynaphthalene-1,4-diol结构式

2-((2R,3R,4R,5S...

(2R,3R,4R,5S,6S)-(+)-6-hydroxy-4-(N-methoxycarbonyl-N-methylamino)-3,5-bis(methoxymethyloxy)-2-methyl-2-(1,4,5,8-tetramethoxy-2-naphthalenyl)tetrahydropyran结构式

(2R,3R,4R,5S,6S...

~%

2-((2R,3R,4R,5S,6R)-4-(dimethylamino)-3,5,6-tris(methoxymethoxy)-2-methyltetrahydro-2H-pyran-2-yl)-5,8-dimethoxynaphthalene-1,4-diol结构式

2-((2R,3R,4R,5S...

(2R,3R,4S,5S)-(-)-6-(tert-butyldimethylsilyloxy)-4-(N-methoxycarbonyl-N-methylamino)-3,5-bis(methoxymethyloxy)-2-(1,4,5,8-tetramethoxy-2-naphthalenyl)-2-hexanol结构式

(2R,3R,4S,5S)-(...

~%

2-((2R,3R,4R,5S,6R)-4-(dimethylamino)-3,5,6-tris(methoxymethoxy)-2-methyltetrahydro-2H-pyran-2-yl)-5,8-dimethoxynaphthalene-1,4-diol结构式

2-((2R,3R,4R,5S...

(2R,3R,4S,5S)-(-)-6-(tert-butyldimethylsilyloxy)-4-(N-methoxycarbonyl-N-methylamino)-3,5-bis(methoxymethyloxy)-2-(1,4,5,8-tetramethoxy-2-naphthalenyl)-2-hexanol结构式

(2R,3R,4S,5S)-(...

~%

(2R,3R,4R,5S,6R)-(-)-4-dimethylamino-3,5,6-tris(methoxymethyloxy)-2-methyl-2-(1,4,5,8-tetramethoxy-2-naphthalenyl)tetrahydropyran结构式

(2R,3R,4R,5S,6R...

(2S,3S,4R,5R)-(-)-3-(N-methoxycarbonyl-N-methylamino)-2,4-bis(methoxymethyloxy)-5-(1,4,5,8-tetramethoxy-2-naphthalenyl)-1,5-hexanediol结构式

(2S,3S,4R,5R)-(...

~%

(2R,3R,4R,5S,6R)-(-)-4-dimethylamino-3,5,6-tris(methoxymethyloxy)-2-methyl-2-(1,4,5,8-tetramethoxy-2-naphthalenyl)tetrahydropyran结构式

(2R,3R,4R,5S,6R...

(3S,4R,5R,6R)-4-(N-methoxycarbonyl-N-methylamino)-3,5-bis(methoxymethyloxy)-6-methyl-6-(1,4,5,8-tetramethoxy-2-naphthalenyl)tetrahydro-2-pyranone结构式

(3S,4R,5R,6R)-4...

~%

(2R,3R,4R,5S,6R)-(-)-4-dimethylamino-3,5,6-tris(methoxymethyloxy)-2-methyl-2-(1,4,5,8-tetramethoxy-2-naphthalenyl)tetrahydropyran结构式

(2R,3R,4R,5S,6R...

(2R,3R,4R,5S,6S)-(+)-6-hydroxy-4-(N-methoxycarbonyl-N-methylamino)-3,5-bis(methoxymethyloxy)-2-methyl-2-(1,4,5,8-tetramethoxy-2-naphthalenyl)tetrahydropyran结构式

(2R,3R,4R,5S,6S...

~%

(2R,3R,4R,5S,6R)-(-)-4-dimethylamino-3,5,6-tris(methoxymethyloxy)-2-methyl-2-(1,4,5,8-tetramethoxy-2-naphthalenyl)tetrahydropyran结构式

(2R,3R,4R,5S,6R...

(2R,3R,4S,5S)-(-)-6-(tert-butyldimethylsilyloxy)-4-(N-methoxycarbonyl-N-methylamino)-3,5-bis(methoxymethyloxy)-2-(1,4,5,8-tetramethoxy-2-naphthalenyl)-2-hexanol结构式

(2R,3R,4S,5S)-(...

~95%

(2S,3S,4R,5R)-(-)-3-(N-methoxycarbonyl-N-methylamino)-2,4-bis(methoxymethyloxy)-5-(1,4,5,8-tetramethoxy-2-naphthalenyl)-1,5-hexanediol结构式

(2S,3S,4R,5R)-(...

(2R,3R,4S,5S)-(-)-6-(tert-butyldimethylsilyloxy)-4-(N-methoxycarbonyl-N-methylamino)-3,5-bis(methoxymethyloxy)-2-(1,4,5,8-tetramethoxy-2-naphthalenyl)-2-hexanol结构式

(2R,3R,4S,5S)-(...

~%

(2R,3R,4R,5S,6R)-(+)-2-(5,8-dimethoxy-1,4-dioxo-2-naphthalenyl)-4-dimethylamino-3,5,6-tris(methoxymethyloxy)-2-methyltetrahydropyran结构式

(2R,3R,4R,5S,6R...

(2S,3S,4R,5R)-(-)-3-(N-methoxycarbonyl-N-methylamino)-2,4-bis(methoxymethyloxy)-5-(1,4,5,8-tetramethoxy-2-naphthalenyl)-1,5-hexanediol结构式

(2S,3S,4R,5R)-(...

~%

(2R,3R,4R,5S,6R)-(+)-2-(5,8-dimethoxy-1,4-dioxo-2-naphthalenyl)-4-dimethylamino-3,5,6-tris(methoxymethyloxy)-2-methyltetrahydropyran结构式

(2R,3R,4R,5S,6R...

(3S,4R,5R,6R)-4-(N-methoxycarbonyl-N-methylamino)-3,5-bis(methoxymethyloxy)-6-methyl-6-(1,4,5,8-tetramethoxy-2-naphthalenyl)tetrahydro-2-pyranone结构式

(3S,4R,5R,6R)-4...

~%

(2R,3R,4R,5S,6R)-(+)-2-(5,8-dimethoxy-1,4-dioxo-2-naphthalenyl)-4-dimethylamino-3,5,6-tris(methoxymethyloxy)-2-methyltetrahydropyran结构式

(2R,3R,4R,5S,6R...

(2R,3R,4R,5S,6R)-(-)-4-(N-methoxycarbonyl-N-methylamino)-3,5,6-tris(methoxymethyloxy)-2-methyl-2-(1,4,5,8-tetramethoxy-2-naphthalenyl)tetrahydropyran结构式

(2R,3R,4R,5S,6R...

~%

(2R,3R,4R,5S,6R)-(+)-2-(5,8-dimethoxy-1,4-dioxo-2-naphthalenyl)-4-dimethylamino-3,5,6-tris(methoxymethyloxy)-2-methyltetrahydropyran结构式

(2R,3R,4R,5S,6R...

(2R,3R,4R,5S,6S)-(+)-6-hydroxy-4-(N-methoxycarbonyl-N-methylamino)-3,5-bis(methoxymethyloxy)-2-methyl-2-(1,4,5,8-tetramethoxy-2-naphthalenyl)tetrahydropyran结构式

(2R,3R,4R,5S,6S...

~%

(2R,3R,4R,5S,6R)-(+)-2-(5,8-dimethoxy-1,4-dioxo-2-naphthalenyl)-4-dimethylamino-3,5,6-tris(methoxymethyloxy)-2-methyltetrahydropyran结构式

(2R,3R,4R,5S,6R...

(2R,3R,4S,5S)-(-)-6-(tert-butyldimethylsilyloxy)-4-(N-methoxycarbonyl-N-methylamino)-3,5-bis(methoxymethyloxy)-2-(1,4,5,8-tetramethoxy-2-naphthalenyl)-2-hexanol结构式

(2R,3R,4S,5S)-(...

~%

(2R,3R,4R,5S,6S)-(+)-6-hydroxy-4-(N-methoxycarbonyl-N-methylamino)-3,5-bis(methoxymethyloxy)-2-methyl-2-(1,4,5,8-tetramethoxy-2-naphthalenyl)tetrahydropyran结构式

(2R,3R,4R,5S,6S...

(2S,3S,4R,5R)-(-)-3-(N-methoxycarbonyl-N-methylamino)-2,4-bis(methoxymethyloxy)-5-(1,4,5,8-tetramethoxy-2-naphthalenyl)-1,5-hexanediol结构式

(2S,3S,4R,5R)-(...

~%

(2R,3R,4R,5S,6S)-(+)-6-hydroxy-4-(N-methoxycarbonyl-N-methylamino)-3,5-bis(methoxymethyloxy)-2-methyl-2-(1,4,5,8-tetramethoxy-2-naphthalenyl)tetrahydropyran结构式

(2R,3R,4R,5S,6S...

(3S,4R,5R,6R)-4-(N-methoxycarbonyl-N-methylamino)-3,5-bis(methoxymethyloxy)-6-methyl-6-(1,4,5,8-tetramethoxy-2-naphthalenyl)tetrahydro-2-pyranone结构式

(3S,4R,5R,6R)-4...

~%

(2R,3R,4R,5S,6S)-(+)-6-hydroxy-4-(N-methoxycarbonyl-N-methylamino)-3,5-bis(methoxymethyloxy)-2-methyl-2-(1,4,5,8-tetramethoxy-2-naphthalenyl)tetrahydropyran结构式

(2R,3R,4R,5S,6S...

(2R,3R,4S,5S)-(-)-6-(tert-butyldimethylsilyloxy)-4-(N-methoxycarbonyl-N-methylamino)-3,5-bis(methoxymethyloxy)-2-(1,4,5,8-tetramethoxy-2-naphthalenyl)-2-hexanol结构式

(2R,3R,4S,5S)-(...

~%

(3S,4R,5R,6R)-4-(N-methoxycarbonyl-N-methylamino)-3,5-bis(methoxymethyloxy)-6-methyl-6-(1,4,5,8-tetramethoxy-2-naphthalenyl)tetrahydro-2-pyranone结构式

(3S,4R,5R,6R)-4...