THE CHROMIUM-REFORMATSKY REACTION - ASYMMETRIC-SYNTHESIS OF THE ALDOLFRAGMENT OF THE CYTOTOXIC EPOTHILONS FROM 3-(2-BROMOACYL)-2-OXAZOLIDINONES

Authors
GABRIEL T WESSJOHANN L
Citation
T. Gabriel et L. Wessjohann, THE CHROMIUM-REFORMATSKY REACTION - ASYMMETRIC-SYNTHESIS OF THE ALDOLFRAGMENT OF THE CYTOTOXIC EPOTHILONS FROM 3-(2-BROMOACYL)-2-OXAZOLIDINONES, Tetrahedron letters, 38(8), 1997, pp. 1363-1366
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
8
Year of publication
1997
Pages
1363 - 1366
Database
ISI
SICI code
0040-4039(1997)38:8<1363:TCR-AO>2.0.ZU;2-I
Abstract
In a two step, one pot reaction of 4-benzyl oxazolidinone, 2-bromoacet yl halide, chromium dichloride and a suitable 3-oxo-aldehyde derivativ e the C1-C6-Me-fragment of epothilons is available in its correct oxid ation state and enantiomeric form. Compared to common methods, the chr omium-Reformatsky variation preferentially yields the opposite diaster eomers and gives improved chemo- and diastereoselection. (C) 1997 Else vier Science Ltd.