The first total synthesis of potent antitumoral (±)-mafaicheenamine A, unnatural 6-fluoromafaicheenamine A and expedient synthesis of clausine E

Abstract

The first total synthesis of potent antitumoral mafaicheenamine A (1) and its unnatural analogue, 6-fluoromafaicheenamine A (2) have been accomplished.

Catalytic Function of Cu (I) and Cu (II) in Total Synthesis of Alkaloids

“…[202] The first total synthesis of 321 was achieved and reported by Ullah and co-workers in 2016. [203] The synthesis of 321 was started from market purchasable, ester 317, which converted into the desired 318 after N-arylation under Barton reaction conditions using phenylead triacetate in the presence of Cu(II) acetate. The latter was subjected to cyclodehydrogenation in AcOH, using Pd(II) acetate to give the desired compound 319.…”

Synthesis of Thymidine Phosphorylase Inhibitor Based on Quinoxaline Derivatives and Their Molecular Docking Study

“…TP performs the same function as platelet endothelial cell growth factor (PD-ECGF) [11,12]. TP belonging to mammalians shares 39% sequence similarity with TP of E. coli , while the enzyme of mammalians also shares 65% resemblance with the active sites of residues of E. coli enzyme [13]. The production of 2′-deoxy- d -ribose can be limited through TP inhibitors which in turn suffocate the growth of tumor cells [14,15].…”

Total synthesis of naturally occurring 1-oxygenated carbazole alkaloids - clausine E, clausenapin, indizoline and formal synthesis of clausenaline D

“…Yield: 0. 19 Methyl 1-methoxy-2-(3-methylbut-2-en-1-yl)-9H-carbazole-3-carboxylate (10). A flamedried, 2-necked round bottomed flask under argon atmosphere was charged with triphenylphosphonium isopropyl iodide (0.58 g, 0.00134 mol) and anhydrous THF (10 mL).…”

“…18 Ullah and coworkers reported the synthesis of intermediate 10 using palladium catalysed O-prenylation of clausine E and subsequent microwave assisted oClaisen rearrangement. 19 Clausine E was synthesized using palladium acetate catalyzed cyclodehydrogenation of methyl 3-(benzyloxy)-4-(phenylamino) benzoate as the key step. 19 Intermediate 10 was utilized for accomplishing the first total synthesis of (±)-mafaicheenamine A. Chang and coworkers described synthesis of the intermediate 10 using O-allylation of clausine E and olefin metathesis as the key steps and used it as a precursor for getting indizoline.…”

“…19 Clausine E was synthesized using palladium acetate catalyzed cyclodehydrogenation of methyl 3-(benzyloxy)-4-(phenylamino) benzoate as the key step. 19 Intermediate 10 was utilized for accomplishing the first total synthesis of (±)-mafaicheenamine A. Chang and coworkers described synthesis of the intermediate 10 using O-allylation of clausine E and olefin metathesis as the key steps and used it as a precursor for getting indizoline. Further they also synthesized Clausenapin, claulansine M and clausenaline D from clausine E. 20 Clausine E was synthesized by TFAA-mediated annulation of (E)-4-(1′H-indol-3′-yl)-3-(methoxycarbonyl)but-3-enoic acid, obtained from Stobbe condensation of indole-3-carbaldehyde, 21 with dimethyl succinate using sodium hydride as a base.…”