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Access to Enantiopure 2,5‐Diaryltetrahydrofurans – Application to the Synthesis of (–)‐Virgatusin and (+)‐Urinaligran
Author(s) -
Martinet Sophie,
Méou Alain,
Brun Pierre
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900099
Subject(s) - enantiopure drug , chemistry , catalysis , catalytic hydrogenation , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , enantioselective synthesis
The diastereoselective Mn III ‐promoted radical addition of β‐oxoesters 1 onto N ‐cinnamoyloxazolidinones 2 afforded 2,3‐dihydrofurans 3 . After catalytic hydrogenation of the C=C bond, followed by reductive removal of the chiral auxiliary, the resulting enantiopure tetrahydrofurans 5 were transformed in two steps into naturally occurring (–)‐virgatusin and (+)‐urinaligran and two other, nonnatural, tetrasubstituted THF lignans. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)