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Concise total synthesis of the prolyl endopeptidase inhibitor eurystatin A via a novel Passerini reaction–deprotection–acyl migration strategy

✍ Scribed by Timothy D Owens; Gian-Luca Araldi; Ruth F Nutt; J.Edward Semple

Book ID: 104231344
Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 98 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)01287-4

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✦ Synopsis

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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