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The chemistry of 2h‐3,1‐benzoxazine‐2,4(1H)‐dione (isatoic anhydride). 17 Synthesis of 2‐alkyl‐4‐quinolone alkaloids via a one‐step reaction of N‐methylisatoic anhydride with methyl ketone enolates

1985; Wiley; Volume: 22; Issue: 2 Linguagem: Inglês

10.1002/jhet.5570220256

1943-5193

Gary M. Coppola,

Cancer therapeutics and mechanisms

Abstract Lithium enolates derived from aliphatic methyl ketones react with N ‐methylisatoic anhydride (5) at −78° to give 2‐alkyl‐4‐quinolone alkaloids 7 in a single step. The method was used to synthesize both double bond isomers of 1‐methyl‐2‐(8‐tridecenyl‐4(1 H )‐quinolinone (8) thereby showing that the alkaloid evocarpine possesses the Z‐olefin stereochemistry 8a. Reduction of 8a provided the alkaloid dihydroevocarpine (16). Compound 16 was also directly prepared from the reaction of 5 with the lithium enolate of 2‐pentadecanone.