Regioselective synthesis of islandicin and digitopurpone

JR Wiseman, JJ Pendery, CA Otto…

Index: Wiseman, John R.; Pendery, John J.; Otto, Charlotte A.; Chiong, Kaolin G. Journal of Organic Chemistry, 1980 , vol. 45, # 3 p. 516 - 519

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Citation Number: 22

Abstract

Renewed interest i: n the synthesis of the anthraquinone pigments islandicin (la)'and digitopurpone (1b) 2 has been aroused since these substances bear a substitution pattern reminisecnt of the clinically important anthracyclinones daunomycinone and adriamycinone (2b). 4 Recently, total syntheses5 of these compounds and some

 Related Synthetic Route
1,4-dihydroxy-3-methyl-5-methoxyanthracene-9,10-dione Structure

68047-75-6

1,4-dihydroxy-3...

~52%

Digitopurpone Structure

34425-57-5

Digitopurpone

2-(bromomethyl)-3-(dibromomethyl)anisole Structure

71785-97-2

2-(bromomethyl)...

~%

Digitopurpone Structure

34425-57-5

Digitopurpone

2-methyl-8-methoxy-1,4-anthraquinone Structure

71785-95-0

2-methyl-8-meth...

~%

Digitopurpone Structure

34425-57-5

Digitopurpone

1,4-diacetoxy-5-methoxy-3-methylanthracene Structure

71785-99-4

1,4-diacetoxy-5...

~%

Digitopurpone Structure

34425-57-5

Digitopurpone

1,4-dihydroxy-5-methoxy-2-methylanthracene-9,10-dione Structure

71786-00-0

1,4-dihydroxy-5...

~87%

9,10-Anthracenedione,1,4,5-trihydroxy-2-methyl- Structure

476-56-2

9,10-Anthracene...

2-(bromomethyl)-3-(dibromomethyl)anisole Structure

71785-97-2

2-(bromomethyl)...

~%

9,10-Anthracenedione,1,4,5-trihydroxy-2-methyl- Structure

476-56-2

9,10-Anthracene...

2-methyl-5-methoxy-1,4-anthraquinone Structure

71785-94-9

2-methyl-5-meth...

~%

9,10-Anthracenedione,1,4,5-trihydroxy-2-methyl- Structure

476-56-2

9,10-Anthracene...

1,4-diacetoxy-5-methoxy-2-methylanthracene Structure

71785-98-3

1,4-diacetoxy-5...

~%

9,10-Anthracenedione,1,4,5-trihydroxy-2-methyl- Structure

476-56-2

9,10-Anthracene...

2-(bromomethyl)-3-(dibromomethyl)anisole Structure

71785-97-2

2-(bromomethyl)...

~%

1,4-dihydroxy-5-methoxy-2-methylanthracene-9,10-dione Structure

71786-00-0

1,4-dihydroxy-5...

1,4-diacetoxy-5-methoxy-2-methylanthracene Structure

71785-98-3

1,4-diacetoxy-5...

~%

1,4-dihydroxy-5-methoxy-2-methylanthracene-9,10-dione Structure

71786-00-0

1,4-dihydroxy-5...

2-methyl-5-methoxy-1,4-anthraquinone Structure

71785-94-9

2-methyl-5-meth...

~%

1,4-dihydroxy-5-methoxy-2-methylanthracene-9,10-dione Structure

71786-00-0

1,4-dihydroxy-5...

Furan Structure

110-00-9

Furan

~%

4-METHOXYISOBENZOFURAN-1(3H)-ONE Structure

4792-33-0

4-METHOXYISOBEN...


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