Access to Enantiopure 2,5‐Diaryltetrahydrofurans – Application to the Synthesis of (–)‐Virgatusin and (+)‐Urinaligran | Zendy

Martinet Sophie | Zendy; Méou Alain | Zendy; Brun Pierre | Zendy

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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)

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