A new efficient route for multigram asymmetric synthesis of alkannin and shikonin

…, AT Strongilos, VP Papageorgiou…

Index: Couladouros, Elias A.; Strongilos, Alexandros T.; Papageorgiou, Vassilios P.; Plyta, Zoi F. Chemistry - A European Journal, 2002 , vol. 8, # 8 p. 1795 - 1803

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Citation Number: 26

Abstract

Abstract A short and convergent approach for the synthesis of alkannin, shikonin and shikalkin is presented. A Hauser-type annulation of cyanophthalide 26 with enone 7 affords the complete aromatic system in just one step with concomitant attachment of the entire side chain. Subsequent Corey's oxazaborolidine mediated asymmetric reduction of the above advanced intermediate, leads to the required isomer in high enantiomeric excess. Finally, ...

 Related Synthetic Route
POTASSIUM CYANIDE Structure

151-50-8

POTASSIUM CYANIDE

3,3-Dimethylallyl bromide Structure

870-63-3

3,3-Dimethylall...

~84%

4-Methyl-3-pentenenitrile Structure

4786-23-6

4-Methyl-3-pent...

4-Methyl-3-pentenenitrile Structure

4786-23-6

4-Methyl-3-pent...

~87%

4-methylpent-3-enoic acid Structure

504-85-8

4-methylpent-3-...

3,3-Dimethylallyl bromide Structure

870-63-3

3,3-Dimethylall...

~%

4-methylpent-3-enoic acid Structure

504-85-8

4-methylpent-3-...

4-methylpent-3-enoic acid Structure

504-85-8

4-methylpent-3-...

~%

Shikonine Structure

517-89-5

Shikonine

4-Methyl-3-pentenenitrile Structure

4786-23-6

4-Methyl-3-pent...

~%

Shikonine Structure

517-89-5

Shikonine

6-methyl-hepta-1,5-dien-3-one Structure

33698-69-0

6-methyl-hepta-...

~%

Shikonine Structure

517-89-5

Shikonine

3,3-Dimethylallyl bromide Structure

870-63-3

3,3-Dimethylall...

~%

Shikonine Structure

517-89-5

Shikonine

N-methoxy-N,4-dimethylpent-3-enamide Structure

206996-05-6

N-methoxy-N,4-d...

~%

Shikonine Structure

517-89-5

Shikonine

N/A Structure

443686-72-4

N/A

~%

Shikonine Structure

517-89-5

Shikonine

N/A Structure

443686-71-3

N/A

~%

Shikonine Structure

517-89-5

Shikonine

2-(1'-hydroxy-4'-methylpent-3'-en-1'-yl)-5,8-dimethoxy-1,4-naphthaquinone Structure

145668-25-3

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

~%

Shikonine Structure

517-89-5

Shikonine

1-(1,4-dihydroxy-5,8-dimethoxynaphthalen-2-yl)-4-methylpent-3-en-1-one Structure

443686-50-8

1-(1,4-dihydrox...

~%

Shikonine Structure

517-89-5

Shikonine

2-(1-hydroxy-4-methylpent-3-en-1-yl)-5,8-dimethoxynaphthalene-1,4-diol Structure

443686-67-7

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

~%

Shikonine Structure

517-89-5

Shikonine

N/A Structure

97476-17-0

N/A

~87%

2-SULFO-1,4-BENZENEDICARBOXYLIC ACID 1,4-DIMETHYL ESTER, SODIUM SALT Structure

88818-28-4

2-SULFO-1,4-BEN...

1,4-dihydroxy-5,8-dimethoxy-2-naphthonitrile Structure

197573-93-6

1,4-dihydroxy-5...

~%

2-SULFO-1,4-BENZENEDICARBOXYLIC ACID 1,4-DIMETHYL ESTER, SODIUM SALT Structure

88818-28-4

2-SULFO-1,4-BEN...


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