Asymmetric Radical Synthesis of 2,5‐Diaryl‐2,3‐dihydrofurans − Application to the Preparation of (+)‐Phyltetralin | Zendy

Garzino Frédéric | Zendy; Méou Alain | Zendy; Brun Pierre | Zendy

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Asymmetric Radical Synthesis of 2,5‐Diaryl‐2,3‐dihydrofurans − Application to the Preparation of (+)‐Phyltetralin

Author(s) -

Garzino Frédéric,

Méou Alain,

Brun Pierre

Publication year - 2003

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.200390198

Subject(s) - chemistry , enantiopure drug , radical cyclization , enantioselective synthesis , lignan , stereochemistry , chiral auxiliary , organic chemistry , medicinal chemistry , combinatorial chemistry , catalysis

The diastereoselective Mn III ‐promoted radical addition of β‐oxo ester 1 onto N ‐cinnamoyloxazolidinone 2 affords, after removal of the chiral auxiliary, the enantiopure 2,5‐diaryl‐2,3‐dihydrofuran (−)‐ 4 . Its SnCl 4 ‐induced rearrangement leads to a 4‐aryltetralone immediate precursor of the aryltetralin lignan (+)‐phyltetralin ( 9 ). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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