Recent Progress in the Synthesis of Carbazolequinone Natural Products

doi:10.6023/cjoc202412020

Abstract

Carbazolequinone natural products have attracted extensive attention due to their good antimalarial, antitumor, and antiviral biological activities, making them a prominent research target in the field of medicinal chemistry. The synthesis strategies of carbazolequinone compounds are summarized in the past three decades, mainly including transition metal catalysis (palladium, copper, ruthenium, etc.), transition metal-free catalysis and oxidation reaction methods, which can be used to synthesize carbazolequinone compounds in a concise and efficient manner. Moreover, future research directions are envisioned, including the development of more efficient catalytic systems, expansion of substrate scope and advancement of green synthesis methods. These efforts aim to broaden the application prospects of carbazolequinone compounds in drug development. Finally, an in-depth exploration of their structure-activity relationships provides novel strategies and insights for the discovery and design of new drugs based on the carbazolequinone scaffold.

Key words: carbazolequinone, natural product, total synthesis, biological activity

Cite this article

Baichuan Mo, Tingting Li, Fang Wang, Xiaojie Li, Darifu Ba. Recent Progress in the Synthesis of Carbazolequinone Natural Products[J]. Chinese Journal of Organic Chemistry, 2025, 45(8): 2746-2766.

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Fig. & Tab. 52

Figure 1. Representive carbazolequinone natural products

Scheme 1. Synthesis of carbazolequinones by Pd-catalyzed oxidative cyclization

Scheme 2. Pd-catalyzed oxidative coupling of 5-anilino-2-phenylthio-1,4-benzoquinones to prepare carbazolequinones

Scheme 3. Regioselective addition of arylamines to 2-methyl-1,4-benzoquinone

Scheme 4. Two sequential Pd-catalyzed synthesis of murrayaquinone A

Scheme 5. Pd-catalyzed microwave-assisted synthesis of carbazolequinones

Scheme 6. Kusurkar’s group synthetic route to calothrixin B

Scheme 7. Ishikura’s group synthetic route to calothrixin A and calothrixin B

Scheme 8. Nagarajan’s group synthetic route to calothrixin A and calothrixin B

Scheme 9. Sieveking’s group prepared carbazoloquinones

Scheme 10. Kaliyaperumal’s group synthetic route to calothrixin B

Scheme 11. Kaliyaperumal’s group synthetic route to murrayaquinone A

Scheme 12. Hibino’s group synthetic route to carbazolequinones

Scheme 13. Synthetic route for the preparation of o-carbocar- bazolequinones

Scheme 14. Strategies for Pd-catalyzed synthesis of carbazoquinones

Scheme 15. Plausible mechanism for Pd-catalyzed C—H arylation

Scheme 16. Clift’s group synthetic route to calothrixin B and calothrixin A

Scheme 17. Liu’s group synthetic route to calothrixin B

Scheme 18. Synthesis of calothrixin A and calothrixin B

Scheme 19. Synthetic route toward murrayaquionne A

Scheme 20. Synthesis of carbazolequinones by Pd-catalyzed double arylation

Scheme 21. Pd-catalyzed intramolecular cyclization for synthesis of carbazoloquinones

Scheme 22. Pd-catalyzed coupling synthesis of carbazoloquinones

Scheme 23. Pd catalyzed synthesis of various substituted carbazolequinones

Scheme 24. Visible-light-induced Pd-catalyzed synthesis of carbazolequinones

Scheme 25. Proposed mechanism for visible-light-promoted Pd-catalyzed C—H

Scheme 26. CuCl2-catalyzed synthesis of murrayaquinone A

Scheme 27. Copper-catalyzed intramolecular cyclization of aminonaphthoquinone for the synthesis of carbazolequinones

Scheme 28. Total synthesis of calothrixin B via Sonogashira coupling/copper-catalyzed oxidative cyclization

Scheme 29. Total synthesis of calothrixin B via Suzuki cross-coupling and copper-catalyzed reaction

Scheme 30. Synthesis of murrayaquinone A via tandem ring-closing metathesis and dehydrogenation reaction

Scheme 31. Synthesis of carbazolequinones via tandem ring-closing metathesis and dehydrogenation reaction

Scheme 32. Synthesis route of ellipticine quinones

Scheme 33. Synthesis of carbazolequinones using FeCl3-mediated domino reaction protocol

Scheme 34. Total synthesis of calothrixin A and calothrixin B

Scheme 35. Iridium-catalyzed conversion of carbazole to carbazolequinone

Scheme 36. Rh(III)-catalyzed cross-coupling of quinones with arenes to prepare carbazolequinones

Scheme 37. Gold catalyzed oxidative cyclization of terminal diynes to carbazolequinones

Scheme 38. Base-promoted synthesis of carbazolequinones from furoindolones and aryne

Scheme 39. Mal’s group synthetic route for calothrixin B

Scheme 40. Synthesis of carbazolequinone by Hauser annulation of furoindolones

Scheme 41. Synthesis of carbazolequinones via formal [3＋2] cycloaddition of arynes and 2-aminophenanthridinedione

Scheme 42. Synthesis of carbazolequinones by formal [3＋2] cycloaddition of arynes and 2-aminoquinones

Scheme 43. Preparation of carbazomycin G by oxidation of [bis(trifluoroacetoxy)iodo]benzene

Scheme 44. Route for the synthesis of murrayaquinone A

Scheme 45. Total synthesis of carbazomycin G

Scheme 46. Dethe’s group synthetic route to calothrixin B

Scheme 47. Nagarajan’s group synthetic route to calothrixin B

Scheme 48. Cheon’s group synthetic route to calothrixin B

Scheme 49. Pabbaraja’s group synthetic route to calothrixin B

Scheme 50. Iodine oxidation of brominated Fischer-Borsche rings to carbazolequinones

Scheme 51. Iodine/periodic acid oxidation of Fischer-Borsche rings to carbazolequinones

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