Total synthesis of (.+-.)-14-epicorynoline,(.+-.)-corynoline, and (.+-.)-6-oxocorynoline

M Cushman, A Abbaspour…

Index: Cushman, Mark; Abbaspour, Aziz; Gupta, Yash Pal Journal of the American Chemical Society, 1983 , vol. 105, # 9 p. 2873 - 2879

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Citation Number: 43

Abstract

Abstract: The condensation of piperonylidenemethylamine (15) with 3, 4-(methylenedioxy)-7- methylhomophthalic anhydride (14) has been utilized as the key step in a total synthesis of the naturally occurring hexahydrobenzo [c] phenanthridine alkaloids (*)-corynoline (l),(*)-6- oxmrynoline (2), and (*)-14-epicorynoline (3). The production of each of the desired diastereomers 16 and 17 was maximized under certain specified reaction conditions. An ...