373604-97-8Relevant articles and documents
Concise total synthesis of the prolyl endopeptidase inhibitor eurystatin A via a novel Passerini reaction-deprotection-acyl migration strategy
Owens, Timothy D,Araldi, Gian-Luca,Nutt, Ruth F,Semple
, p. 6271 - 6274 (2001)
The Passerini reaction between suitably protected alaninal, leucine isonitrile, and ornithine components delivered adducts 10a,b in high yield. Orthogonal N-deprotection of 10a led, via a smooth O- to N-acyl migration, to 11, which constitutes the entire skeleton of the eurystatins. Subsequent deprotection, macrocyclization, elaboration, and final oxidation steps efficiently afforded eurystatin A 1a in high overall yield.