Concise total synthesis of the prolyl endopeptidase inhibitor eurystatin A via a novel Passerini reaction–deprotection–acyl migration strategy
Tetrahedron Letters(2001)
摘要
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.
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关键词
total synthesis
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