Tumor inhibitors. LXXXVII. Total synthesis of the tumor-inhibitory alkaloid thalicarpine

…, AJ Liepa, V Kameswaran, K Sempuku

Index: Kupchan; Liepa; Kameswaran; Sempuku Journal of the American Chemical Society, 1973 , vol. 95, # 9 p. 2995 - 3000

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Citation Number: 18

Abstract

Abstract: An efficient total synthesis of thalicarpine (13b), a tumor-inhibitory aporphine benzylisoquinoline alkaloid, is described. The diaryl ether (Sa), prepared from lb and 4a, was condensed with the 3, 4-dihydroisoquinolinium salt 2a to give 9a. Reduction of 9a, followed by diazotization in phosphoric acid and heating, yielded the aporphine 10a and the phenol 9h. Formylation of 10a gave (+)-hernandaline (lob), which was resolved with (+)-a- ...