SELECTIVE OXIDATION OF LIGNAN COMPOUNDS BY DIMETHYLDIOXIRANE - DIASTEREOSELECTIVE OPENING OF ASARININ FURO-FURAN SKELETON

Authors
MINCIONE E SANETTI A BERNINI R FELICI M BOVICELLI P
Citation
E. Mincione et al., SELECTIVE OXIDATION OF LIGNAN COMPOUNDS BY DIMETHYLDIOXIRANE - DIASTEREOSELECTIVE OPENING OF ASARININ FURO-FURAN SKELETON, Tetrahedron letters, 39(47), 1998, pp. 8699-8702
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
47
Year of publication
1998
Pages
8699 - 8702
Database
ISI
SICI code
0040-4039(1998)39:47<8699:SOOLCB>2.0.ZU;2-Y
Abstract
Asarinin, a furo-furan lignan compound with two benzyl-ethereal carbon s of opposite stereochemistry, was monooxidised at a selected centre b y DMD to a chiral substituted tetrahydrofuran. Use of a dilute solutio n of DMD was crucial for the success of the process. The stereochemist ry of the product was confirmed by a similar oxidation of sesamin, the C-7' isomer of asarinin (C) 1998 Elsevier Science Ltd. All rights res erved.