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Cyclic peptides I (R = benzyl, allyl; R1 = NO2, NH2, H), which contain the macrocyclic aryl ether skeleton of some naturally occurring alkaloids such as pandamine, were prepd. Key to the synthetic strategy was the cyclocondensation of the linear peptides II [NR2 = NHBOC, N(benzyl)2, N(allyl)2; R2 = SiMe2CMe3, H] to form macrocycles I. Thus, II [NR2 = N(allyl)2, R2 = H] in a DMF soln. was treated with Bu4N+F- in the presence of mol. sieves to form I (R = allyl, R1 = NO2), which was subsequently converted first to the amine I (R = allyl, R1 = NH2) and then to the target macrocycle I (R = allyl, R1 = H). [on SciFinder (R)]
Christian Heinis, Jonas Alfred Karl Wilbs, Simon Jan Middendorp
Christian Heinis, Xinjian Ji, Edward Will, Anne Sofie Luise Zarda, Alessandro Angelini, Alexander Lund Nielsen, Manuel Leonardo Merz, Mischa Schüttel, Ganesh Kumar Mothukuri, Zsolt Bognár