New Pyridone Approach:  Total Synthesis of Mappicine Ketone (Nothapodytine B)

Abstract

A novel synthesis of mappicine ketone, which possesses strong selective activity against the herpes viruses HSV-1 and HSV-2, including those Acyclovir-resistant, and human cytomegalovirus (HCMV) has been efficiently accomplished. The synthesis highlights a new pyridone approach that effectively combines a double, intramolecular Michael addition in a conjugated ester-conjugated amide with oxidation-decarboxylation of the resulting piperidone.

An efficient total synthesis of the pyrroquinazolinoquinoline alkaloid, Luotonin A, employing an intramolecular hetero Diels–Alder reaction

“…In practice, 3-(aminomethyl)-2-bromoquinoline (7) 8 was coupled with benzoic acid (8) in the presence of benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluoro-phosphate (BOP) to afford the amide 9 in 92% yield. Introduction of the cyano group at the C-2 position of the bromide 7 was next performed using Sakamoto and Ohsawa's protocol, 9 and the desired cyanide 10 was obtained in 97% yield.…”

“…After removal of the solvent under reduced pressure, the crude product was chromatographed. Elution with a 2:1 mixture of 1H,d,J=7.5 Hz),7.09 (1H,ddd,J=8.5,7.0,1.0 Hz),7.47 (1H,ddd,J=9.0,7.5,1.5 Hz),7.56 (1H,ddd,J=8.0,6.0,1.5 Hz),7.71 (1H,ddd,J=9.0,7.0,1.5 Hz),7.82 (1H,d,J=7. 8,56.0,111.4,116.6,120.6,121.3,128.0,128.7,129.6,130.9,132.3,133.4,133.8,133.9,137.4,147.3,157.9,165.9. HRMS m/z: C 19 …”

Cascade cyclization of 1-(2-yl-3-phenylprop-2-enyl)-6-oxo-1,6-dihydropyridine-2-carbonitrile radical: Mechanistic insights from DFT study

“…A wide variety of approaches to these alkaloids and their derivatives have been developed [19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38], which focused on constructing ring-fused molecular skeletons, as shown in Scheme 1.…”

New Synthetic Methods to 2-Pyridone Rings

“…Greene and col. have used a new approach based on a doubly effectivel intramolecular Michael addition of a conjugated esterconjugated amide with oxidation-decarboxylation [91]. Greene and col. have used a new approach based on a doubly effectivel intramolecular Michael addition of a conjugated esterconjugated amide with oxidation-decarboxylation [91].…”