Solid supported high-throughput organic synthesis of peptide beta-turn mimetics via Petasis reaction/diketopiperazine formation

Authors
Golebiowski, A Klopfenstein, SR Chen, JJ Shao, X
Citation
A. Golebiowski et al., Solid supported high-throughput organic synthesis of peptide beta-turn mimetics via Petasis reaction/diketopiperazine formation, TETRAHEDR L, 41(25), 2000, pp. 4841-4844
Citations number
11
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
25
Year of publication
2000
Pages
4841 - 4844
Database
ISI
SICI code
0040-4039(20000619)41:25<4841:SSHOSO>2.0.ZU;2-O
Abstract
High-throughput organic synthesis of bicyclic diketopiperazines 1, beta-tur n mimetics, is described. Starting from Merrifield resin-bound piperazine-2 -carboxylic acid, first two (R-4 and R-5) Side chains are introduced via th e Petasis reaction and subsequent amide bond formation. Unblocking the a-am ino group of piperazine-2-carboxylic acid, Boc-N-protected alpha-amino acid coupling and deprotection followed by cyclative cleavage introduces the re maining R-2 and R-1 side chains. (C) 2000 Elsevier Science Ltd. All rights reserved.