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Synthesis of Shikalkin (±Shikonin) and Related Compounds

…, Y Tanoue, A Hatada, H Sakamoto

文献索引：Terada; Tanoue; Hatada; Sakamoto Bulletin of the Chemical Society of Japan, 1987 , vol. 60, # 1 p. 205 - 213

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被引用次数: 75

摘要

The key intermediate, 2-formyl-1, 4, 5, 8-tetramethoxynaphthalene, was prepared through 1, 4, 5, 8-tetramethoxynaphthalene, which was obtained from 1, 5-naphthalenediol via three steps or from naphthazarin via one step. A total synthesis of shikalkin and dihydroshikalkin have been accomplished with this aldehyde via a side-chain introductions with Grignard reactions and the following demethylations.

1,4,5,8-tetramethoxynaphthalene结构式

1,4,5,8-tetrame...

~%

2-(1-hydroxy-4-methylpentyl)-5,8-dimethoxynaphthalene-1,4-dione结构式

2-(1-hydroxy-4-...

1,5-dibromo-4,8-dimethoxynaphthalene结构式

1,5-dibromo-4,8...

~%

2-(1-hydroxy-4-methylpentyl)-5,8-dimethoxynaphthalene-1,4-dione结构式

2-(1-hydroxy-4-...

1,4,5,8-四甲氧基萘-2-甲醛结构式

1,4,5,8-四甲氧基萘-2-甲醛

~%

2-(1-hydroxy-4-methylpentyl)-5,8-dimethoxynaphthalene-1,4-dione结构式

2-(1-hydroxy-4-...

1,4-Naphthalenedione,5,8-dimethoxy-结构式

1,4-Naphthalene...

~%

2-(1-hydroxy-4-methylpentyl)-5,8-dimethoxynaphthalene-1,4-dione结构式

2-(1-hydroxy-4-...

1,5-二甲氧基萘结构式

1,5-二甲氧基萘

~%

2-(1-hydroxy-4-methylpentyl)-5,8-dimethoxynaphthalene-1,4-dione结构式

2-(1-hydroxy-4-...

2-(1-hydroxy-4-methylpentyl)-5,8-dimethoxynaphthalene-1,4-dione结构式

2-(1-hydroxy-4-...

~25%

紫草烷结构式

5,8-dihydroxy-2-(1-hydroxy-4-methylpentyl)-1,4-naphthoquinone结构式

5,8-dihydroxy-2...

1,4-Naphthalenedione,5,8-dimethoxy-结构式

1,4-Naphthalene...

~%

紫草烷结构式

1,5-二甲氧基萘结构式

1,5-二甲氧基萘

~%

紫草烷结构式

1,4,5,8-tetramethoxynaphthalene结构式

1,4,5,8-tetrame...

~%

紫草烷结构式

1,5-dibromo-4,8-dimethoxynaphthalene结构式

1,5-dibromo-4,8...

~%

紫草烷结构式

1,4,5,8-四甲氧基萘-2-甲醛结构式

1,4,5,8-四甲氧基萘-2-甲醛

~%

紫草烷结构式

2-(1-hydroxy-4-methylpentyl)-1,4,5,8-tetramethoxynaphthalene结构式

2-(1-hydroxy-4-...

~%

紫草烷结构式

甲基碘化镁结构式

甲基碘化镁

5-hydroxy-5-(1,4,5,8-tetramethoxynaphthalen-2-yl)pentan-2-one结构式

5-hydroxy-5-(1,...

~86%

4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pentane-1,4-diol结构式

4-methyl-1-(1,4...

1,4,5,8-tetramethoxynaphthalene结构式

1,4,5,8-tetrame...

~%

4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pentane-1,4-diol结构式

4-methyl-1-(1,4...

1,5-dibromo-4,8-dimethoxynaphthalene结构式

1,5-dibromo-4,8...

~%

4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pentane-1,4-diol结构式

4-methyl-1-(1,4...

1,4-Naphthalenedione,5,8-dimethoxy-结构式

1,4-Naphthalene...

~%

4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pentane-1,4-diol结构式

4-methyl-1-(1,4...

1,5-二甲氧基萘结构式

1,5-二甲氧基萘

~%

4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pentane-1,4-diol结构式

4-methyl-1-(1,4...

1,4,5,8-四甲氧基萘-2-甲醛结构式

1,4,5,8-四甲氧基萘-2-甲醛

~%

4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pentane-1,4-diol结构式

4-methyl-1-(1,4...

2-(4,4-(ethylenedioxy)-1-hydroxypentyl)-1,4,5,8-tetramethoxynaphthalene结构式

2-(4,4-(ethylen...

~%

4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pentane-1,4-diol结构式

4-methyl-1-(1,4...

1,4,5,8-tetramethoxynaphthalene结构式

1,4,5,8-tetrame...

~%

2-(1,4-dihydroxy-4-methylpentyl)-5,8-dimethoxynaphthalene-1,4-dione结构式

2-(1,4-dihydrox...

1,5-dibromo-4,8-dimethoxynaphthalene结构式

1,5-dibromo-4,8...

~%

2-(1,4-dihydroxy-4-methylpentyl)-5,8-dimethoxynaphthalene-1,4-dione结构式

2-(1,4-dihydrox...

1,4,5,8-四甲氧基萘-2-甲醛结构式

1,4,5,8-四甲氧基萘-2-甲醛

~%

2-(1,4-dihydroxy-4-methylpentyl)-5,8-dimethoxynaphthalene-1,4-dione结构式

2-(1,4-dihydrox...

1,4-Naphthalenedione,5,8-dimethoxy-结构式

1,4-Naphthalene...

~%

2-(1,4-dihydroxy-4-methylpentyl)-5,8-dimethoxynaphthalene-1,4-dione结构式

2-(1,4-dihydrox...

1,5-二甲氧基萘结构式

1,5-二甲氧基萘

~%

2-(1,4-dihydroxy-4-methylpentyl)-5,8-dimethoxynaphthalene-1,4-dione结构式

2-(1,4-dihydrox...

5-hydroxy-5-(1,4,5,8-tetramethoxynaphthalen-2-yl)pentan-2-one结构式

5-hydroxy-5-(1,...

~%

2-(1,4-dihydroxy-4-methylpentyl)-5,8-dimethoxynaphthalene-1,4-dione结构式

2-(1,4-dihydrox...

2-(4,4-(ethylenedioxy)-1-hydroxypentyl)-1,4,5,8-tetramethoxynaphthalene结构式

2-(4,4-(ethylen...

~%

2-(1,4-dihydroxy-4-methylpentyl)-5,8-dimethoxynaphthalene-1,4-dione结构式

2-(1,4-dihydrox...

2-(1,4-dihydroxy-4-methylpentyl)-5,8-dimethoxynaphthalene-1,4-dione结构式

2-(1,4-dihydrox...

~27%

2-(1,4-dihydroxy-4-methylpentyl)-5,8-dihydroxynaphthalene-1,4-dione结构式

2-(1,4-dihydrox...

1,4,5,8-tetramethoxynaphthalene结构式

1,4,5,8-tetrame...

~%

2-(1,4-dihydroxy-4-methylpentyl)-5,8-dihydroxynaphthalene-1,4-dione结构式

2-(1,4-dihydrox...

1,4,5,8-四甲氧基萘-2-甲醛结构式

1,4,5,8-四甲氧基萘-2-甲醛

~%

2-(1,4-dihydroxy-4-methylpentyl)-5,8-dihydroxynaphthalene-1,4-dione结构式

2-(1,4-dihydrox...

4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pentane-1,4-diol结构式

4-methyl-1-(1,4...

~%

2-(1,4-dihydroxy-4-methylpentyl)-5,8-dihydroxynaphthalene-1,4-dione结构式

2-(1,4-dihydrox...

1,4-Naphthalenedione,5,8-dimethoxy-结构式

1,4-Naphthalene...

~%

2-(1,4-dihydroxy-4-methylpentyl)-5,8-dihydroxynaphthalene-1,4-dione结构式

2-(1,4-dihydrox...

1,5-二甲氧基萘结构式

1,5-二甲氧基萘

~%

2-(1,4-dihydroxy-4-methylpentyl)-5,8-dihydroxynaphthalene-1,4-dione结构式

2-(1,4-dihydrox...

5-hydroxy-5-(1,4,5,8-tetramethoxynaphthalen-2-yl)pentan-2-one结构式

5-hydroxy-5-(1,...

~%

2-(1,4-dihydroxy-4-methylpentyl)-5,8-dihydroxynaphthalene-1,4-dione结构式

2-(1,4-dihydrox...

1,5-dibromo-4,8-dimethoxynaphthalene结构式

1,5-dibromo-4,8...

~%

2-(1,4-dihydroxy-4-methylpentyl)-5,8-dihydroxynaphthalene-1,4-dione结构式

2-(1,4-dihydrox...

2-(4,4-(ethylenedioxy)-1-hydroxypentyl)-1,4,5,8-tetramethoxynaphthalene结构式

2-(4,4-(ethylen...

~%

2-(1,4-dihydroxy-4-methylpentyl)-5,8-dihydroxynaphthalene-1,4-dione结构式

2-(1,4-dihydrox...

1,4-Naphthalenedione,5,8-dimethoxy-结构式

1,4-Naphthalene...

硫酸二甲酯结构式

硫酸二甲酯

~46%

1,4,5,8-tetramethoxynaphthalene结构式

1,4,5,8-tetrame...

硫酸二甲酯结构式

硫酸二甲酯

5,8-二羟基-1,4-萘醌结构式

5,8-二羟基-1,4-萘醌

~%

1,4,5,8-tetramethoxynaphthalene结构式

1,4,5,8-tetrame...

2-(4,4-(ethylenedioxy)-1-hydroxypentyl)-1,4,5,8-tetramethoxynaphthalene结构式

2-(4,4-(ethylen...

~87%

5-hydroxy-5-(1,4,5,8-tetramethoxynaphthalen-2-yl)pentan-2-one结构式

5-hydroxy-5-(1,...

1,4-Naphthalenedione,5,8-dimethoxy-结构式

1,4-Naphthalene...

~%

5-hydroxy-5-(1,4,5,8-tetramethoxynaphthalen-2-yl)pentan-2-one结构式

5-hydroxy-5-(1,...

1,5-二甲氧基萘结构式

1,5-二甲氧基萘

~%

5-hydroxy-5-(1,4,5,8-tetramethoxynaphthalen-2-yl)pentan-2-one结构式

5-hydroxy-5-(1,...

1,4,5,8-tetramethoxynaphthalene结构式

1,4,5,8-tetrame...

~%

5-hydroxy-5-(1,4,5,8-tetramethoxynaphthalen-2-yl)pentan-2-one结构式

5-hydroxy-5-(1,...

1,5-dibromo-4,8-dimethoxynaphthalene结构式

1,5-dibromo-4,8...

~%

5-hydroxy-5-(1,4,5,8-tetramethoxynaphthalen-2-yl)pentan-2-one结构式

5-hydroxy-5-(1,...

1,4,5,8-四甲氧基萘-2-甲醛结构式

1,4,5,8-四甲氧基萘-2-甲醛

~%

5-hydroxy-5-(1,4,5,8-tetramethoxynaphthalen-2-yl)pentan-2-one结构式

5-hydroxy-5-(1,...

1,5-dibromo-4,8-dimethoxynaphthalene结构式

1,5-dibromo-4,8...

~%

5,8-二羟基-1,4-萘醌结构式

5,8-二羟基-1,4-萘醌

2-(1-methoxy-4-methyl-3-pentenyl)-1,4,5,8-tetramethoxynaphthalene结构式

2-(1-methoxy-4-...

~4%

naphthazarin-dimethyl-hydrofuran hdfr结构式

naphthazarin-di...

1,4,5,8-四甲氧基萘-2-甲醛结构式

1,4,5,8-四甲氧基萘-2-甲醛

~%

naphthazarin-dimethyl-hydrofuran hdfr结构式

naphthazarin-di...

1,4,5,8-tetramethoxynaphthalene结构式

1,4,5,8-tetrame...

~%

naphthazarin-dimethyl-hydrofuran hdfr结构式

naphthazarin-di...

1,4-Naphthalenedione,5,8-dimethoxy-结构式

1,4-Naphthalene...

~%

naphthazarin-dimethyl-hydrofuran hdfr结构式

naphthazarin-di...

1,5-二甲氧基萘结构式

1,5-二甲氧基萘

~%

naphthazarin-dimethyl-hydrofuran hdfr结构式

naphthazarin-di...

1,5-dibromo-4,8-dimethoxynaphthalene结构式

1,5-dibromo-4,8...

~%

naphthazarin-dimethyl-hydrofuran hdfr结构式

naphthazarin-di...

2-(4-hydroxy-1-methoxy-4-methylpentyl)-1,4,5,8-tetramethoxynaphthalene结构式

2-(4-hydroxy-1-...

~%

naphthazarin-dimethyl-hydrofuran hdfr结构式

naphthazarin-di...

2-(1-methoxy-4-oxopentyl)-1,4,5,8-tetramethoxynaphthalene结构式

2-(1-methoxy-4-...

~%

naphthazarin-dimethyl-hydrofuran hdfr结构式

naphthazarin-di...

2-(4,4-(ethylenedioxy)-1-hydroxypentyl)-1,4,5,8-tetramethoxynaphthalene结构式

2-(4,4-(ethylen...

~%

naphthazarin-dimethyl-hydrofuran hdfr结构式

naphthazarin-di...

1,5-dibromo-4,8-dimethoxynaphthalene结构式

1,5-dibromo-4,8...

~%

1,4,5,8-四甲氧基萘-2-甲醛结构式

1,4,5,8-四甲氧基萘-2-甲醛

1,4-Naphthalenedione,5,8-dimethoxy-结构式

1,4-Naphthalene...

~%

1,4,5,8-四甲氧基萘-2-甲醛结构式

1,4,5,8-四甲氧基萘-2-甲醛

1,5-二甲氧基萘结构式

1,5-二甲氧基萘

~%

1,4,5,8-四甲氧基萘-2-甲醛结构式

1,4,5,8-四甲氧基萘-2-甲醛

Total synthesis of shikalkin [(±)-shikonin]

[Terada, Akira; Tanoue, Yasuhiro; Hatada, Akira; Sakamoto, Hiroshi Journal of the Chemical Society, Chemical Communications, 1983 , # 18 p. 987 - 988]

Total synthesis of shikalkin [(±)-shikonin]

[Terada, Akira; Tanoue, Yasuhiro; Hatada, Akira; Sakamoto, Hiroshi Journal of the Chemical Society, Chemical Communications, 1983 , # 18 p. 987 - 988]