Benzyne cyclization route to benzo [c] phenanthridine alkaloids. Synthesis of chelerythrine, decarine, and nitidine

…, P Balakrishnan, KK Sawal, T Mohammad…

Index: Kessar, Satinder V.; Gupta, Yash P.; Balakrishnan, Prasanna; Sawal, Kewal K.; Mohammad, Taj; Dutt, Mahesh Journal of Organic Chemistry, 1988 ,  vol. 53,  # 8  p. 1708 - 1713

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Citation Number: 56

Abstract

The alkaloids chelerythrine (8b) and decarine (74 have been synthesized through a benzyne-mediated cyclization of N-(2-halobenzyl)-l-naphthylamines 4 with KNHz in a" onia/ether. The 7-hydroxybenzo [c] phenanthridine structure 16a proposed for the alkaloid fagaridine is questioned on the basis of comparison with a model compound (16b) synthesized by benzyne cyclization. For the 8, 9-oxygenated alkaloids like nitidine (89, ...