LEWIS-ACID CATALYZED DIELS-ALDER REACTION OF 3-PHENYLTHIO-2-QUINOLINONES WITH SILOXYDIENE - SYNTHESIS OF THE INTERMEDIATE FOR DYNEMICIN-A CORE

Authors
NAGATA T KOIDE Y NARA K ITOH E ARISAWA M NARUTO S TORISAWA Y HINO T NAKAGAWA M
Citation
T. Nagata et al., LEWIS-ACID CATALYZED DIELS-ALDER REACTION OF 3-PHENYLTHIO-2-QUINOLINONES WITH SILOXYDIENE - SYNTHESIS OF THE INTERMEDIATE FOR DYNEMICIN-A CORE, Chemical and Pharmaceutical Bulletin, 44(2), 1996, pp. 451-453
Citations number
18
Categorie Soggetti
Pharmacology & Pharmacy",Chemistry
Journal title
Chemical and Pharmaceutical Bulletin → ACNP
ISSN journal
00092363
Volume
44
Issue
2
Year of publication
1996
Pages
451 - 453
Database
ISI
SICI code
0009-2363(1996)44:2<451:LCDRO3>2.0.ZU;2-R
Abstract
Preparation of the 1-methoxycarbonyl-3-phenylthio-2-quinolinone (10) f rom dihydro-2-quinolinone (5) and its Diels-Alder reaction with 2-trim ethylsilyloxy-1, 3-butadiene under Lewis acid catalyst is described. C onversion of the D-A adduct (11) to 9-phenanthridinone ketal (16) will open a new synthetic route to a dynemicin A core structure.