Premium
Synthesis of new deuterium‐labelled lignanolactones
Author(s) -
Leppälä Eija,
Pohjoispää Monika,
Koskimies Jorma,
Wähälä Kristiina
Publication year - 2008
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.1553
Subject(s) - chemistry , deuterium , reagent , hydrogen–deuterium exchange , medicinal chemistry , organic chemistry , hydrogen , physics , quantum mechanics
Abstract Deuteration of several lignanolactones, using 2 H 3 PO 4 ·BF 3 / 2 H 2 O as the deuteration reagent, is described, affording new stable isotopically pure polydeuterated lignans. All aromatic hydrogens are exchanged, including the less active ones. The order of 1 H/ 2 H exchange is studied by comparing calculated electrostatic potential values and experimental observations. Labile deuteriums are exchanged back to hydrogens with methanolic HCl to achieve stable isotopically pure compounds. Copyright © 2008 John Wiley & Sons, Ltd.