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

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

Preparation of the 1-methoxycarbonyl-3-phenylthio-2-quinolinone (10) from dihydro-2-quinolinone (5) and its Diels-Alder reaction with 2-trimethylsilyloxy-1, 3-butadiene under Lewis acid catalyst is described. Conversion of the D-A adduct (11) to 9-phenenthridinone ketal (16) will open a new syntheti...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1996/02/15, Vol.44(2), pp.451-453
Hauptverfasser: NAGATA, Toshiaki, KOIDE, Yuuki, NARA, Kazumasa, ITOH, Etsuko, ARISAWA, Mitsuhiro, NARUTO, Shunji, TORISAWA, Yasuhiro, HINO, Tohru, NAKAGAWA, Masako
Format: Artikel
Sprache:eng
Schlagworte:
2-quinolinone
Chemistry
Diels-Alder reaction
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Lewis acid
Organic chemistry
phenanthridine
Preparations and properties
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Zusammenfassung:Preparation of the 1-methoxycarbonyl-3-phenylthio-2-quinolinone (10) from dihydro-2-quinolinone (5) and its Diels-Alder reaction with 2-trimethylsilyloxy-1, 3-butadiene under Lewis acid catalyst is described. Conversion of the D-A adduct (11) to 9-phenenthridinone ketal (16) will open a new synthetic route to a dynemicin A core structure.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.44.451