STEREOSELECTIVE SYNTHESIS OF FLAVONOIDS .4. TRANS-DIHYDROFLAVONOLS AND CIS-DIHYDROFLAVONOLS

Authors
VANRENSBURG H VANHEERDEN PS BEZUIDENHOUDT BCB FERREIRA D
Citation
H. Vanrensburg et al., STEREOSELECTIVE SYNTHESIS OF FLAVONOIDS .4. TRANS-DIHYDROFLAVONOLS AND CIS-DIHYDROFLAVONOLS, Tetrahedron, 53(41), 1997, pp. 14141-14152
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
41
Year of publication
1997
Pages
14141 - 14152
Database
ISI
SICI code
0040-4020(1997)53:41<14141:SSOF.T>2.0.ZU;2-D
Abstract
Epoxidation of a series of poly-oxygenated chalcones with H2O2 in the presence of poly-alpha-aminoacids yielded chiral aromatic oxygenated o xiranes in moderate to high optical yields. Lewis acid-catalysed pheny lmethanethiol ringopening of the epoxide functionality and subsequent formation of the pyranone heterocycle, afforded Irons-and cis-dihydrof lavonols in moderate to high enantiomeric excess and field. (C) 1997 E lsevier Science Ltd.