A new synthesis of the benzo[c]phenanthridines nornitidine, noravicine, and isodecarine, based on a microwave-assisted electrocyclic reaction of the aza 6π-electron system

Total synthesis of benzo[c]phenanthridine alkaloids based on a microwave-assisted electrocyclic reaction of the aza 6π-electron system and structural revision of broussonpapyrine

“…13 C NMR (75 MHz, CD 3 OD) d: 52.0, 57. 8, 60.9, 104.2, 105.0, 106.2, 118.2, 120.7, 121.4, 123.2, 125.7, 129.4, 131.1, 132.0, 134.4, 134.8, 146.3, 150.3, 151.2, 155.8, 162.4.…”

“…11 Recently, we reported the total synthesis of furoisoquinoline, 12a phenanthridine, 12b bcarboline, 12c azaanthraquinone, 12d and benzo [c]phenanthridine 13 alkaloids based on a microwave (MW)-assisted electrocyclic reaction of the aza 6p-electron system. We here describes the full detailed synthesis of benzo [c]phenanthridines 1aef, and 2f as depicted in Fig.…”

Total Synthesis of Two 8‐Oxoprotoberberine Alkaloids: Alangiumkaloids A and B

“…We have been interested in the unique structure and pharmacological action of condensed heteroaromatic compounds, which includes those that are natural products, and have achieved the total synthesis of several heteroaromatic compounds (e.g., scorpinone, calothrixins, benzo[ c ]phenanthridines, cassiarin C, dichotomines, marinacarbolines, and isocryptolepine) by using an electrocyclic reaction of the 6π‐electron system as our original method . Moreover, we have been searching for highly active compounds based on these naturally occurring compounds and their derivatives .…”

Dual behavior of 2‐tetralone: A new approach for the synthesis of 5‐aryl‐7,8,13,14‐tetrahydrodibenzo[a,i]phenanthridine

“…The literature preparations of the phenanthridine ring system have disadvantages, such as, lengthy syntheses, low yields, and structurally complicated precursors [8, 15–20]. Even a synthesis involving a few steps from simple precursors such as formaldehyde and 2‐methylbenzonitrile affords benzo[c]phenanthridine in a 6% overall yield [15].…”