Quinolinone alkaloids

Chiral butyrolactones of type 27 and 28 have substantial value in asymmetric synthesis because they contain readily differentiable difunctional group relationships e.g. 1,5-di-carboxylic acid, 1,4-hydroxy carboxylic acid, 1,6-hydroxy-carboxylic acid, 1,6-diol etc.) that would be difficult to assemble by existing asymmetric condensation and pericyclic processes. Applications of these chiral derivatives of glutaric acid to syntheses of indole, indoline and quinolinone alkaloids are illustrated in Schemes 16-18. 

He, J., Lion, U., Saltier, L, Gollmick, F. A., Grabley, S., Cai, J., Meiners, M., Schiinke, H., Schaumann, K., Dechert, U. and Krohn, M. 2005. Diastereomeric quinolinone alkaloids from the marine-derived fungus Penicillium janczewskii. Journal of Natural Products, 68 1397-1399. 

A considerable number of new quinoline and acridone alkaloids has been identified and the recognition of two new groups of dimeric quinolinone alkaloids is of particular interest. There has been little activity in the quinazoline alkaloid area and this section is omitted this year. 

I. 5 Dimeric Quinolinone Alkaloids.- The first dimeric quinolinone alkaloids, pteledimerine and the closely related pteledimeridine, are constituents of Ptelea trifoliate (cf. Vol. 10, p.80 and Vol. 

Hoelzel SCSM, Vieira ER, Giacomelli SR, Dalcol II, Zanatta N, Mrael AF. An unusual quinolinone alkaloid from Waltheria douradinha. Phytochemistry 2005 66 1163-7. 

Quinoline-based dmgs, 215-216 Quinolinic acid, 125 Quinolinone alkaloids, 68-70 Quinolinone methyl-penicinoline,... 

JURD, L., R.Y. WONG. 1981. New quinolinone alkaloids from the heartwood of Euxylophora paraensis. Aust. 

Staerk D, Kesting JR, Sairafianpour M, Witt M, Asili J, Emami SA, Jaroszewski JW (2009) Accelerated dereplication of crude extracts using HPLC-PDA-MS-SPE-NMR quinolinone alkaloids of Haplophyllum acutifolium. Phytochemistry 70 1055-1061... 

Lavaud C, Massiot G, Vasquez C et al (1995) 4-Quinolinone alkaloids fiom Dictyoloma peruviana. Phytochemistry 40 317—320... 

The alkaloid dubamine contains a single bond between the two heteroarene units. This lond was formed in 79% yield by the generally valuable palladium-catalyzed eoupling of an ryltrimethylstannane with an aryl triflate (see section 1.6). The requisite stannane was pre-ared from l,3-benzodioxol-5-yl triflate and hexamethyldistannane with the same palladium atalyst, the triflate ester was obtained from 2(1 f/)-quinolinone and trifluoromethanesulfonic jihydride (A.M. Echavarren, 1987). An earlier attempt to perform this aryl coupling by dassical means gave a yield of only 1 %. 

Alkylation of isoquinolinone by Michael reaction followed by acid-catalyzed cyclization is used to prepare acridine-1,9-diones <97SC95>. The oxidation of these compounds to the 1-hydroxyacridones has been applied to acridine alkaloids <97T12717>. The reaction of the 2-amino-1,3-diene with the quinolinone 52 affords the acridine derivative 53 directly <97JCS(P1)2807>. 

The constituents of the tumorigenic plant Melochia tomentosa include 6-methoxy-7,8-methylenedioxycoumarin, three cyclopeptide alkaloids, melo-chinone (a quinolinone derivative), and two novel phenylpentyl-isatins, melosatins A and B, for which the structures (3) and (4) have been deduced. The structure of melosatin A was confirmed by synthesis (Scheme 1),... 

The second involves construction of the acridone nucleus in the course of the synthesis. The main approaches used in this latter case are very similar to those which permitted access to the simple acridone alkaloids, e.g. (i) cyclization of a diarylamine intermediate, (ii) cyclization of a benzophenone intermediate, or (iii) construction of the acridone system starting from a quinoline or a quinolinone which bring together the A and B or B and C rings of the acridone skeleton. 

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