ChemInform Abstract: Polycyclic Hydroxyquinones. Part 29. Regioselective Reactions of 5- Sulfur-Substituted Furan-2(5H)-one Anions with Naphthoquinone Monoketals. Application to the Synthesis of Anthracyclinone Precursors.

✍ Scribed by P. ASENJO; F. FARINA; M. V. MARTIN; M. C. PAREDES; J. J. SOTO

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 33 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199720040

✦ Synopsis

Polycyclic Hydroxyquinones. Part 29. Regioselective Reactions of 5-Sulfur-Substituted Furan-2(5H)-one Anions with Naphthoquinone Monoketals. Application to the Synthesis of Anthracyclinone Precursors.

-The anions of the furanones (I) react with naphthoquinone monoketals ( II) to afford exclusively the adducts (III). Anellation reactions occur with the anion of (IV) to yield the anthraquinones (VI) and (VII) . These compounds (cf. the methyl derivative (VIII) of (VI)) can be used for Diels-Alder reactions with butadienes to afford tetracyclic systems.

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