AN INSIGHT INTO THE T-BUTYLBROMIDE DIMETHYL-SULFOXIDE REAGENT - A NOVEL APPLICATION IN LIGNAN TOTAL SYNTHESIS

Authors
HARROWVEN DC DENNISON ST
Citation
Dc. Harrowven et St. Dennison, AN INSIGHT INTO THE T-BUTYLBROMIDE DIMETHYL-SULFOXIDE REAGENT - A NOVEL APPLICATION IN LIGNAN TOTAL SYNTHESIS, Tetrahedron letters, 34(20), 1993, pp. 3323-3326
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
20
Year of publication
1993
Pages
3323 - 3326
Database
ISI
SICI code
0040-4039(1993)34:20<3323:AIITTD>2.0.ZU;2-6
Abstract
A novel aromatisation sequence initiated by the t-butylbromide - dimet hyl sulfoxide reagent is presented. The unprecedented conversion of th e dithianes 1 and 3 to the aryl sulfides 6 and 7 has lead to the synth esis of the naturally occuring 9-deoxyarylnaphthalene lignans taiwanin C and 1,2,3,4-dehydrodeoxypodophyllotoxin and gives a useful insight into the mechanism by which this unusual reagent acts.