Journal
TETRAHEDRON LETTERS
Volume 50, Issue 47, Pages 6519-6521Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2009.09.034
Keywords
3,4-Dihydroxyphenylalanine (DOPA); Catechol moiety; IBX; Polymer-supported IBX (IBX polystyrene); Regioselective aromatic hydroxylation
Categories
Funding
- Ministero dell'Universita e della Ricerca Scientifica e Tecnologica
- PNR-FIRB
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An efficient route to 3,4-dihydroxylphenylalanine (DOPA) and DOPA pept des was described by oxidation of L-tyrosine and L-tyrosine derivatives with 2-iodoxybenzoic acid (IBX) DOPA was obtained after ail Situ reduction of the corresponding ortho-Cl U I none with sodium dithionite. Oxidation reactions proceeded Ill good yields and high chemo- and regio-selectivity The chirality of the DOPA residue was retained under the reaction conditions The efficiency and the selectivity of the reaction were successfully tested using recyclable polymer-supported IBX (C) 2009 Elsevier Ltd. All rights reserved
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