Studies on the syntheses of heterocyclic compounds. Part DCXXII. Total synthesis of (±)-mappicine [7-(1-hydroxypropyl)-8-methyl-indolizino[1,2-b]quinolin-9(11H)-one]

Abstract

Methyl 9,11-dihydro-9-oxoindolizino[1,2-b]quinoline-7-carboxylate (4) was converted into its 8-methyl derivative (5), reduction of which gave 7-hydroxymethyl-8-methylindolizino[1,2-b]quinolin-9(11H)-one (9). This was converted into (±)-mappicine (1) by way of the 7-carbaldehyde (13) and the 7-propionyl derivative (14).