The Barton radical decarboxylation on solid phase. A versatile synthesis of peptides containing modified amino acids

Authors
Attardi, ME Taddei, M
Citation
Me. Attardi et M. Taddei, The Barton radical decarboxylation on solid phase. A versatile synthesis of peptides containing modified amino acids, TETRAHEDR L, 42(20), 2001, pp. 3519-3522
Citations number
24
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
20
Year of publication
2001
Pages
3519 - 3522
Database
ISI
SICI code
0040-4039(20010514)42:20<3519:TBRDOS>2.0.ZU;2-E
Abstract
Barton esters were prepared starting from different carboxylic acids loaded on a Wang resin. Light induced fragmentation occurred giving a radical tha t reacted with CBrCl3 to give the corresponding bromides, whereas conjugate addition to electron-poor alkenes proved to be less synthetically useful. The bromides so formed were further functionalised on the resin with differ ent nucleophiles. (C) 2001 Elsevier Science Ltd. All rights reserved.