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

Tetrahedron

New and efficient routes for the synthesis of murrayaquinone A and murrayanine

SM Bhosale, AA Momin, RS Kusurkar

Index: Bhosale, Shrikar M.; Momin, Aadil A.; Kusurkar, Radhika S. Tetrahedron, 2012 , vol. 68, # 32 p. 6420 - 6426

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Citation Number: 5

Abstract

Three new routes were established for the synthesis of biologically active murrayaquinone A and a new method was developed for synthesis of murrayanine from the same starting material as 4-hydroxy carbazole. During the synthetic course a few novel observation were recorded, which include two one pot reaction sequences and C–N bond cleavage by sodium cyanoborohydride.

N/A Structure

~72%

murrayaquinone A Structure

murrayaquinone A

9H-Carbazol-4-ol Structure

9H-Carbazol-4-ol

~%

murrayaquinone A Structure

murrayaquinone A

4-hydroxy-9H-carbazole-3-carbaldehyde Structure

4-hydroxy-9H-ca...

~%

murrayaquinone A Structure

murrayaquinone A

N/A Structure

~%

murrayaquinone A Structure

murrayaquinone A

4-hydroxy-9H-carbazole-1-carbaldehyde Structure

4-hydroxy-9H-ca...

~%

murrayaquinone A Structure

murrayaquinone A

1-bromo-4-hydroxy-9H-carbazole-3-carbaldehyde Structure

1-bromo-4-hydro...

~%

murrayaquinone A Structure

murrayaquinone A

(9-benzyl-1,4-dimethoxy-9H-carbazol-3-yl)methanol Structure

(9-benzyl-1,4-d...

~%

murrayaquinone A Structure

murrayaquinone A

N/A Structure

~%

murrayaquinone A Structure

murrayaquinone A

9-benzyl-3-(bromomethyl)-9H-carbazole-1,4-dione Structure

9-benzyl-3-(bro...

~%

murrayaquinone A Structure

murrayaquinone A

3-bromo-4-hydroxy-9H-carbazole-1-carbaldehyde Structure

3-bromo-4-hydro...

~%

murrayaquinone A Structure

murrayaquinone A

N/A Structure

~%

murrayaquinone A Structure

murrayaquinone A

N/A Structure

~%

murrayaquinone A Structure

murrayaquinone A

9-benzyl-4-(benzyloxy)-1-(1,3-dioxan-2-yl)-3-methyl-9H-carbazole Structure

9-benzyl-4-(ben...

~%

murrayaquinone A Structure

murrayaquinone A

1-bromo-9H-carbazole-3-carbaldehyde Structure

1-bromo-9H-carb...

Sodium Methylate Structure

Sodium Methylate

~87%

Dictysine Structure

4-hydroxy-9H-carbazole-3-carbaldehyde Structure

4-hydroxy-9H-ca...

~%

Dictysine Structure

1-bromo-4-hydroxy-9H-carbazole-3-carbaldehyde Structure

1-bromo-4-hydro...

~%

Dictysine Structure

N/A Structure

~%

Dictysine Structure

9H-Carbazol-4-ol Structure

9H-Carbazol-4-ol

~%

Dictysine Structure

New synthesis of carbazole-1, 4-quinone using a tandem ring-...

[Nishiyama, Takashi; Choshi, Tominari; Kitano, Kohdai; Hibino, Satoshi Tetrahedron Letters, 2011 , vol. 52, # 30 p. 3876 - 3878]

New synthesis of carbazole-1, 4-quinone using a tandem ring-...

[Nishiyama, Takashi; Choshi, Tominari; Kitano, Kohdai; Hibino, Satoshi Tetrahedron Letters, 2011 , vol. 52, # 30 p. 3876 - 3878]

New synthesis of carbazole-1, 4-quinone using a tandem ring-...

[Nishiyama, Takashi; Choshi, Tominari; Kitano, Kohdai; Hibino, Satoshi Tetrahedron Letters, 2011 , vol. 52, # 30 p. 3876 - 3878]

Bromoquinone–enaminone annulations: syntheses of murrayaquin...

[Murphy, William S.; Bertrand, Martial Journal of the Chemical Society - Perkin Transactions 1, 1998 , # 24 p. 4115 - 4119]