Synthesis of a novel C2-aryl substituted 1,2-unsaturated pyrrolobenzodiazepine

Abstract

A novel C2-aryl 1,2-unsaturated PBD (14) has been prepared via an enol triflate intermediate (8). The regiochemistry of triflation is dependent upon the point at which the reaction is performed during the synthetic route.

Pyrimidine‐Annulated Pyrrolobenzodiazepines. A New Ring System Related to Aspergillus Alkaloids

“…We started our investigation from the pyrrolo[2,1-c] [1,4] benzodiazepine natural product 4 (from Isatis indigotica [36] ), which is readily available by heating isatoic anhydride 3 at reflux with (S)-proline in DMF by literature procedures. [37,38] Its methylated derivative 5 was obtained analogously by starting from (S)-α-methylproline.…”

“…Special interest is currently focused on new derivatives [1,2,3] that can recognize and bind to specific sequences of DNA [4,5,6,7] and cause a wide variety of potential biological responses. In this context, PDBs are one of the most promising types of lead compounds.…”

“…Pyrrolo [2,1-c] [1,4]benzodiazepines (PBDs) form a class of biologically active compounds. Special interest is currently focused on new derivatives [1,2,3] that can recognize and bind to specific sequences of DNA [4,5,6,7] and cause a wide variety of potential biological responses.…”

Hypervalent Iodine Reagents for the Oxidation of Alcohols and Their Application to Complex Molecule Synthesis

“…(40). [67] This method was found to be superior to that of Swern oxidation in several aspects (high yield, no requirement of anhydrous conditions or an inert atmosphere, etc. ).…”

Speedy and Clean Hypervalent Iodine/Nitroxyl Radical Mediated Oxidation of Alcohols Using Recyclable Adamantane Reagent with Highly Active 2-Azaadamantane-<i>N</i>-oxyl Organocatalyst

“…Due to the salient features of the catalytic conditions as well as the exclusive chemoselectivity toward alcohols in the presence of many oxidation-sensitive functional groups, this mild organocatalytic system has been frequently used for the selective oxidation of alcohol groups in complex molecules, [4][5][6][7][8] as represented by the early examples which appeared in the total synthesis of natural products, such as discodermolide and leucascandrolide A. 12,13) Moreover, significant advances have been developed to date for the reagent and catalyst recycling, making the strategy and method even more attractive. [14][15][16][17][18][19][20][21][22][23] Regarding this interest, we have recently reported a versatile and clean method based on the use of the adamantanetype recyclable hypervalent iodine reagent 1 [24][25][26] (Fig.…”