2-CHLORO-1,3-BUTADIENE AS AN EFFICIENT ENOPHILE IN THE DIELS–ALDER REACTION WITH ANTHRACENE-1,4,9,10-TETRAONE. A SIMPLE SYNTHESIS OF THE 4-DEMETHOXYANTHRACYCLINONE INTERMEDIATE
1984; Oxford University Press; Volume: 13; Issue: 3 Linguagem: Inglês
10.1246/cl.1984.473
ISSN1348-0715
AutoresYoshikazu Kimura, M. SUZUKI, Teruyo Matsumoto, Rumiko Abe, Shiro Terashima,
Tópico(s)Synthesis of Organic Compounds
ResumoAbstract Diels-Alder reaction of 2-chloro-1,3-butadiene with anthracene-1,4,9,10-tetraone was found to occur exclusively at the external(C2,3) double bond, giving the adduct in an excellent yield. The adduct was readily converted to the 4-demethoxyanthracyclinone intermediate, (±)-7-deoxy-4-demethoxydaunomycinone, by way of 5,12-dihydroxy-l,2,3,4-tetrahydronaphthacene-2,6,11-trione.
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