The Journal of Organic Chemistry

Synthesis of the marine alkaloids aaptamine and demethyloxyaaptamine and of the parent structure didemethoxyaaptamine

JC Pelletier, MP Cava

Index: Pelletier, Jeffrey C.; Cava, Michael P. Journal of Organic Chemistry, 1987 , vol. 52, # 4 p. 616 - 622

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Citation Number: 57

Abstract

6, 7-Dimetho~ y-3, 4-dihydroisoquinoline~~ was reacted with 1 equiv of malonic acid (120 OC, neat mixture) to afford the amino acid 13 in 92% yield.* This product cleanly cyclodehydrated in warm PPA to afford the amino ketone 14 (66%). 12 Further transformation of 14 to the sulfonamide 15 went without difficulty (91%). Treatment of either 14 or 15 with NaN3 in H2S0,, however, resulted in complete recovery of starting material. ...