53811-52-2Relevant academic research and scientific papers
Benzyne Cyclization Route to Benzophenanthridine Alkaloids. Synthesis of Chelerythrine, Decarine, and Nitidine
Kessar, Satinder V.,Gupta, Yash P.,Balakrishnan, Prasanna,Sawal, Kewal K.,Mohammad, Taj,Dutt, Mahesh
, p. 1708 - 1713 (2007/10/02)
The alkaloids chelerythrine (8b) and decarine (7c) have been synthesized through a benzyne-mediated cyclization of N-(2-halobenzyl)-1-naphthylamines 4 with KNH2 in ammonia/ether.The 7-hydroxybenzophenanthridine 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 (8i), this cyclization proceeded poorly, but a dramatic improvement occurred when LDA/THF at -78 deg C was used instead of KNH2/NH3.
SYNTHESIS OF SANGUINARINE, CHELERYTHRINE, AND OXYSANGUINARINE
Smidrkal, Jan
, p. 1412 - 1420 (2007/10/02)
Benzophenanthridines Va and Vb have been prepared by photocyclization of amines IVa and IVb and transformed into the alkaloids sanguinarine (VIa) and chelerythrine (VIb).Oxysanguinarine (XIV) has been prepared from diazoketone XVIII.
