Concise total synthesis of the prolyl endopeptidase inhibitor eurystatin Avia a novel Passerini reaction-deprotection-acyl migration strategy

Authors
Owens, TD Araldi, GL Nutt, RF Semple, JE
Citation
Td. Owens et al., Concise total synthesis of the prolyl endopeptidase inhibitor eurystatin Avia a novel Passerini reaction-deprotection-acyl migration strategy, TETRAHEDR L, 42(36), 2001, pp. 6271-6274
Citations number
35
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
36
Year of publication
2001
Pages
6271 - 6274
Database
ISI
SICI code
0040-4039(20010903)42:36<6271:CTSOTP>2.0.ZU;2-F
Abstract
The Passerini reaction between suitably protected alaninal, leucine isonitr ile, and ornithine components delivered adducts 10a,b in high yield. Orthog onal N-deprotection of 10a led, via a smooth O- to N-acyl migration, to 11, which constitutes the entire skeleton of the eurystatins. Subsequent depro tection, macrocyclization, elaboration, and final oxidation steps efficient ly afforded eurystatin A 1a in high overall yield. (C) 2001 Elsevier Scienc e Ltd. All rights reserved.