Loading…
Synthetic study on novel immunosuppressant KF20444
The two new synthetic routes to 6,7-dihydro-10-fluoro-3-(2-fluorophenyl)-5 H- benzo[6,7]cyclohepta[1,2- b]-quinoline-8-carboxylic acid ( 1), a novel immunosuppressant KF20444, are described. The seven-membered ring construction from 2-[4-(2-fluorophenyl)phenyl]-3-(2-carboxyethyl)-4-chloromethyl-6-fl...
Saved in:
Published in: | Bioorganic & medicinal chemistry 2001-12, Vol.9 (12), p.3273-3286 |
---|---|
Main Authors: | , , , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
Summary: | The two new synthetic routes to 6,7-dihydro-10-fluoro-3-(2-fluorophenyl)-5
H- benzo[6,7]cyclohepta[1,2-
b]-quinoline-8-carboxylic acid (
1), a novel immunosuppressant KF20444, are described. The seven-membered ring construction from 2-[4-(2-fluorophenyl)phenyl]-3-(2-carboxyethyl)-4-chloromethyl-6-fluoroquinoline (
17c) was achieved by intramolecular Friedel–Crafts reaction under acidic conditions as the key step. Subsequently, the oxidation of 4-chloromethyl group followed by reduction of carbonyl group on the seven-membered ring afforded
1. This route provides a new method for the synthesis of
1.
A new synthetic route of KF20444, a novel immunosuppressant, is described. The seven-membered ring construction from 2-phenyl-3-(2-carboxyethyl)-4-chloromethylquinoline derivative was achieved by intramolecular Friedel–Crafts reaction as the key step. |
---|---|
ISSN: | 0968-0896 1464-3391 |
DOI: | 10.1016/S0968-0896(01)00238-3 |