Concise total synthesis of water soluble metatacarboline A, C, D, E and F and its anticancer activity

CuBr2-Catalyzed Mild Oxidation of 3,4-Dihydro-β-Carbolines and Application in Total Synthesis of 6-Hydroxymetatacarboline D

“…Nagarajan and his colleagues have recently reported total syntheses of metatacarbolines A, C, D, E, F via the Wittig reaction starting from methyl 1-formyl-β-carboline-3-carboxylate, but 6-hydroxymetatacarboline D 3 , as the most abundant β-carboline alkaloid in M. metata, has not been synthesized yet; thus, we herein developed the first total synthesis of 6-hydroxymetatacarboline D 3 staring from l -5-hydroxy-tryptophan, as depicted in Scheme .…”

Recent Advances in the Synthesis of β-Carboline Alkaloids

“…For the synthesis of the other two marinacarbolines (28 and 30), the ester group of the key intermediate 173 was hydrolyzed, then transformed into an acid chloride (175), which was reacted with tyramine (176) or tryptamine (108) to achieve the synthesis of marinacarboline B (28) and D (30). The simple total synthesis of water-soluble metatacarbolines A (31) and C-F (32-35) has been accomplished starting from β-carboline building blocks 177 [59]. Metatacarboline A was prepared in 3 steps by applying the Wittig reaction of aldehyde 177a with 178, followed by the catalytic reduction of the previously formed double bond and hydrolysis of ester groups to afford the desired product 31 (Scheme 16).…”

1(3)‐Formyl‐β‐carbolines: Potential Aldo‐X Precursors for the Synthesis of β‐Carboline‐Based Molecular Architectures

“…As anticipated, the reaction of n-butyl vinyl ether with isolated aldimine (41)u nder anhydrous conditions afforded the products in superior yields (83-94%). [32] The application of this approach was validated in the total synthesis of the alkaloid nitramarine (45). This synthesis was achieved through the de-esterification of compound 43 by using LiOH, followed by decarboxylation under thermalc onditions to yield nitramarine (Scheme 17).…”

“…[44] Nagarajan and co-workers developed as imple, concise, and protecting-group-free total synthesis of Metatacarboline alkaloids A, C, D, E, and F( 79 and 84)b yu sing 1-formyl-9H-b-carboline (3)a sat emplate. [45] The core framework of the metatacarboline alkaloids was constructed by using ac lassical Wittig reactiono fp hosphonium salt 77 with compounds 3 and 82 to generate the alkene intermediates, which were subjected to catalytic hydrogenation/hydrolysis to yield Metatacarboline alkaloids, as shown in Schemes 28 and 29. These compounds were also evaluated for anticancer activity by using C6 glioma cell lines.…”