Enantiotopical Synthesis of Carbazoquinocins A and D, The Potent Lipid Peroxidation Inhibitors from Streptomyces violaceus 2448-SVT2

Indoloquinones, Part 6. First Palladium-Mediated Oxidative Cyclization of Arylamino-1,2-benzoquinones to Carbazole-3,4-quinones - Application to the Total Synthesis of Carbazoquinocin C and (±)-Carquinostatin A

“…Due to their useful biological activities the carbazole-3,4-quinones became interesting targets for total synthesis. [8][9][10][11][12][13] Ogasawara reported the first synthesis of carbazoquinocin A and D. 8 An electrocyclic ring closure was utilized by Hibino to get access to carbazoquinocins. 9 Based on our iron-mediated construction of the carbazole framework, 3 we described the first total syntheses of carbazoquinocin C, 10 carquinostatin A, 11 and lavanduquinocin.…”

Synthesis and biological evaluation of structural variants of carbazoquinocin C

“…Therefore these novel carbazole alkaloids attracted considerable interest among synthetic organic chemists. Ogasawara reported the first synthesis of the carbazole-3,4-quinones carbazoquinocin A and D [9]. An allene mediated ring closure reaction was used by Hibino et al to produce carbazoquinocins [10].…”

Indoloquinones, Part 7. Total Synthesis of the Potent Lipid Peroxidation Inhibitor Carbazoquinocin C by an Intramolecular Palladium-Catalyzed Oxidative Coupling of an Anilino-1,4-benzoquinone

“…15 In 1996 Ogasawara et al reported the total synthesis of the first members of the carbazoquinocin family, carbazoquinocin A (3a) and carbazoquinocin D (3d). 16 We anticipated that the application of our transition metalmediated and/or -catalyzed processes furnishing the car- bazole nucleus should provide convergent and therefore more simple routes to the carbazoquinocin family.…”