A convenient new route to 4-substituted benzo[de][3,6]phenanthrolin-6(6H)-ones: Important intermediates in the synthesis of ring-A analogues of the cytotoxic marine alkaloid ascididemin.

Authors
Copp, BR Hansen, RP Appleton, DR Lindsay, BS Squire, CJ Clark, GR Rickard, CEF
Citation
Br. Copp et al., A convenient new route to 4-substituted benzo[de][3,6]phenanthrolin-6(6H)-ones: Important intermediates in the synthesis of ring-A analogues of the cytotoxic marine alkaloid ascididemin., SYN COMMUN, 29(15), 1999, pp. 2665-2676
Citations number
11
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNTHETIC COMMUNICATIONS
ISSN journal
00397911 → ACNP
Volume
29
Issue
15
Year of publication
1999
Pages
2665 - 2676
Database
ISI
SICI code
0039-7911(1999)29:15<2665:ACNRT4>2.0.ZU;2-B
Abstract
4-ethylthio- and 4-(4 "-methylphenylthio)benzo[de][3,6]phenanthrolin-6(6H)- one have been synthesised in 4 steps from benzoquinone and then readily con verted to the 4-amino (6d) and 4-methoxy (6c) analogues by nucleophilic sub stitution. Further elaboration of 6d leads to the synthesis of 11-hydroxyas cididemin, which we have found to exhibit antiviral activity in vitro.