COMPOUNDS INTERACTING WITH TUBULIN .1. SY NTHESIS OF ORTHO-ORTHO' SUBSTITUTED PHENYLPYRROLES WITH FREE OR RESTRICTED ROTATION

Authors
ALAZARD JP BOYE O GILLET B GUENARD D BELOEIL JC THAL C
Citation
Jp. Alazard et al., COMPOUNDS INTERACTING WITH TUBULIN .1. SY NTHESIS OF ORTHO-ORTHO' SUBSTITUTED PHENYLPYRROLES WITH FREE OR RESTRICTED ROTATION, Bulletin de la Societe chimique de France, 130(6), 1993, pp. 779-787
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear",Biology,Chemistry
Journal title
Bulletin de la Societe chimique de France → ACNP
ISSN journal
00378968
Volume
130
Issue
6
Year of publication
1993
Pages
779 - 787
Database
ISI
SICI code
0037-8968(1993)130:6<779:CIWT.S>2.0.ZU;2-U
Abstract
The synthesis of ortho-ortho' substituted phenylpyrroles that are susc eptible to isomerization of the biaryl type (atropisomerism) was perfo rmed using a Michael addition of isocyanoacetates with nitrostyrenes. Atropisomerism in phenylpyrroles 14 and 15 was studied by means of H-1 NMR spectroscopy using chiral lanthanide shift reagents (LSR). In th e case of chiral phenylpyrrole 21, an evaluation of the interconversio n parameters between diastereomers (k, DELTAG(T)) was attempted.