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. 2018 Jan 30;140(6):2072–2075. doi: 10.1021/jacs.8b00087

Scheme 1. Synthesis of the Arylomycin Core via Oxidative Macrocyclization.

Scheme 1

Reagents and conditions: (a) 1 (1 equiv), HCl·NH2-Ala-Tyr-OMe (1 equiv), HOBt (1 equiv), EDC (1.5 equiv), Et3N (3.3 equiv), MeCN/DMF, 25 °C (72%); (b) [Cu(MeCN)4][PF6] (2 equiv), TMEDA (2 equiv), O2, MeCN, then 2 (1 equiv), 25 °C (60%). Abbreviations: HOBt = 1-hydroxybenzotriazole, EDC = N-ethyl-N′-(3-(dimethylamino)propyl)carbodiimide hydrochloride, TMEDA = N,N,N′,N′-tetramethylethylenediamine.