e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Synthetic communications

Synthesis of Anthracyclinone Precursor: 5, 12??Dihydroxy??1, 3, 4??trihydronaphthacene??2, 6, 11??quinone

G Tririya, M Zanger

Index: Tririya, Gasirat; Zanger, Murray Synthetic Communications, 2004 , vol. 34, # 17 p. 3047 - 3059

Full Text: HTML

Citation Number: 11

Abstract

Abstract Two practical and efficient approaches for preparing large quantities of 5, 12?? dihydroxy??1, 3, 4??trihydronaphthacene??2, 6, 11??quinone 9 are described. Both synthetic approaches involve a simple route with a fewer number of steps and utilize readily available and inexpensive starting materials. Large??scale production of this precursor may prove to be useful for further research involving the synthesis of antineoplastic anthracyclines and ...

5,8-DIMETHOXY-1,4-DIHYDRO-NAPHTHALENE Structure

5,8-DIMETHOXY-1...

~92%

1a,2,7,7a-Tetrahydro-3,6-dimethoxy-naphth[2,3-b]oxirene Structure

1a,2,7,7a-Tetra...

4A,5,8,8a-Tetrahydro-[1,4]naphthoquinone Structure

4A,5,8,8a-Tetra...

~%

1a,2,7,7a-Tetrahydro-3,6-dimethoxy-naphth[2,3-b]oxirene Structure

1a,2,7,7a-Tetra...

1,4-Naphthalenediol,5,8-dihydro- Structure

1,4-Naphthalene...

~%

1a,2,7,7a-Tetrahydro-3,6-dimethoxy-naphth[2,3-b]oxirene Structure

1a,2,7,7a-Tetra...

1,4-Benzoquinone Structure

1,4-Benzoquinone

~%

1a,2,7,7a-Tetrahydro-3,6-dimethoxy-naphth[2,3-b]oxirene Structure

1a,2,7,7a-Tetra...

Phthalic anhydride Structure

Phthalic anhydride

5,8-Dimethoxy-2-tetralone Structure

5,8-Dimethoxy-2...

~55%

5,12-dihydroxy-3,4-dihydro-1H-tetracene-2,6,11-trione Structure

5,12-dihydroxy-...

1,4-Benzoquinone Structure

1,4-Benzoquinone

~%

5,12-dihydroxy-3,4-dihydro-1H-tetracene-2,6,11-trione Structure

5,12-dihydroxy-...

5,8-DIMETHOXY-1,4-DIHYDRO-NAPHTHALENE Structure

5,8-DIMETHOXY-1...

~%

5,12-dihydroxy-3,4-dihydro-1H-tetracene-2,6,11-trione Structure

5,12-dihydroxy-...

4A,5,8,8a-Tetrahydro-[1,4]naphthoquinone Structure

4A,5,8,8a-Tetra...

~%

5,12-dihydroxy-3,4-dihydro-1H-tetracene-2,6,11-trione Structure

5,12-dihydroxy-...

1,4-Naphthalenediol,5,8-dihydro- Structure

1,4-Naphthalene...

~%

5,12-dihydroxy-3,4-dihydro-1H-tetracene-2,6,11-trione Structure

5,12-dihydroxy-...

N/A Structure

~%

5,12-dihydroxy-3,4-dihydro-1H-tetracene-2,6,11-trione Structure

5,12-dihydroxy-...

1a,2,7,7a-Tetrahydro-3,6-dimethoxy-naphth[2,3-b]oxirene Structure

1a,2,7,7a-Tetra...

~%

5,12-dihydroxy-3,4-dihydro-1H-tetracene-2,6,11-trione Structure

5,12-dihydroxy-...

2-chloro-5,8-dimethoxy-1,4-dihydro-naphthalene Structure

2-chloro-5,8-di...

~%

5,12-dihydroxy-3,4-dihydro-1H-tetracene-2,6,11-trione Structure

5,12-dihydroxy-...

1,4-Naphthalenediol,5,8-dihydro- Structure

1,4-Naphthalene...

Dimethyl sulfate Structure

Dimethyl sulfate

~68%

5,8-DIMETHOXY-1,4-DIHYDRO-NAPHTHALENE Structure

5,8-DIMETHOXY-1...

1,4-Naphthalenediol,5,8-dihydro- Structure

1,4-Naphthalene...

Ethanoic anhydride Structure

Ethanoic anhydride

~95%

(4-acetyloxy-5,8-dihydronaphthalen-1-yl) acetate Structure

(4-acetyloxy-5,...

1,4-Benzoquinone Structure

1,4-Benzoquinone

~%

(4-acetyloxy-5,8-dihydronaphthalen-1-yl) acetate Structure

(4-acetyloxy-5,...

4A,5,8,8a-Tetrahydro-[1,4]naphthoquinone Structure

4A,5,8,8a-Tetra...

~%

(4-acetyloxy-5,8-dihydronaphthalen-1-yl) acetate Structure

(4-acetyloxy-5,...

(4-acetyloxy-5,8-dihydronaphthalen-1-yl) acetate Structure

(4-acetyloxy-5,...

~99%

Naphth[2,3-b]oxirene-3,6-diol, 1a,2,7,7a-tetrahydro-, diacetate Structure

Naphth[2,3-b]ox...

4A,5,8,8a-Tetrahydro-[1,4]naphthoquinone Structure

4A,5,8,8a-Tetra...

~%

Naphth[2,3-b]oxirene-3,6-diol, 1a,2,7,7a-tetrahydro-, diacetate Structure

Naphth[2,3-b]ox...

1,4-Naphthalenediol,5,8-dihydro- Structure

1,4-Naphthalene...

~%

Naphth[2,3-b]oxirene-3,6-diol, 1a,2,7,7a-tetrahydro-, diacetate Structure

Naphth[2,3-b]ox...

1,4-Benzoquinone Structure

1,4-Benzoquinone

~%

Naphth[2,3-b]oxirene-3,6-diol, 1a,2,7,7a-tetrahydro-, diacetate Structure

Naphth[2,3-b]ox...

1a,2,7,7a-Tetrahydro-3,6-dimethoxy-naphth[2,3-b]oxirene Structure

1a,2,7,7a-Tetra...

~42%

5,8-Dimethoxy-2-tetralone Structure

5,8-Dimethoxy-2...

1,4-Benzoquinone Structure

1,4-Benzoquinone

~%

5,8-Dimethoxy-2-tetralone Structure

5,8-Dimethoxy-2...

2-chloro-5,8-dimethoxy-1,4-dihydro-naphthalene Structure

2-chloro-5,8-di...

~23%

5,8-Dimethoxy-2-tetralone Structure

5,8-Dimethoxy-2...

5,8-DIMETHOXY-1,4-DIHYDRO-NAPHTHALENE Structure

5,8-DIMETHOXY-1...

~%

5,8-Dimethoxy-2-tetralone Structure

5,8-Dimethoxy-2...

4A,5,8,8a-Tetrahydro-[1,4]naphthoquinone Structure

4A,5,8,8a-Tetra...

~%

5,8-Dimethoxy-2-tetralone Structure

5,8-Dimethoxy-2...

1,4-Naphthalenediol,5,8-dihydro- Structure

1,4-Naphthalene...

~%

5,8-Dimethoxy-2-tetralone Structure

5,8-Dimethoxy-2...

N/A Structure

~%

5,8-Dimethoxy-2-tetralone Structure

5,8-Dimethoxy-2...

N/A Structure

~87%

1,4-Naphthalenediol,6-chloro-5,8-dihydro- Structure

1,4-Naphthalene...

1,4-Benzoquinone Structure

1,4-Benzoquinone

~%

1,4-Naphthalenediol,6-chloro-5,8-dihydro- Structure

1,4-Naphthalene...

4A,5,8,8a-Tetrahydro-[1,4]naphthoquinone Structure

4A,5,8,8a-Tetra...

~93%

1,4-Naphthalenediol,5,8-dihydro- Structure

1,4-Naphthalene...

1,4-Benzoquinone Structure

1,4-Benzoquinone

~%

1,4-Naphthalenediol,5,8-dihydro- Structure

1,4-Naphthalene...