複素環式化合物の合成研究(第474報)Camptothecin関連化合物の合成研究III.12-Ethyl-6,7,10,12,13,13a-hexahydro-12-hydroxy-1H, 9H-furano[3,4-g]indolo[3,2-d]quinolizineの合成

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12-Ethyl-6,7,10,12,13,13a-hexahydro-12-hydroxy-1H, 9H-furano [3,4-g] indolo [3,2-d] quinolizine (X), a corynantheidine-type indole base, was synthesised as a possible intermediate for the synthesis of camptothecin, as follows. The Perkin reaction of cinchomeronic anhydride with propionic anhydride in the presence of sodium propionate afforded 1-ethylidene-1,3-dihydro-3-oxofurano [4,5-c] pyridine (XII), which was converted to ethyl 4-propionylnicotinate (XV) by esterification. Treatment of XV with ethylene glycol in the presence of p-toluenesulfonic acid at 140°for 4 hr gave β-hydroxyethyl 4-propionyl-nicotinate ethylene ketal (XVI) which was reacted with 3-chloroacetylindole to give the corresponding quaternary pyridinium salt (XVIII). Lithium aluminum hydride reduction of XVIII, followed by acid treatment, gave the expected compound (X).
社団法人日本薬学会の論文
1972-06-25