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Base-catalyzed intramolecular condensation of tokinolide B

✍ Scribed by Beatriz Quiroz-Garcı́a; Liliana Hernández; Rubén A. Toscano; Olov Sterner; Guillermo Delgado

Book ID
104253196
Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
175 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

The novel pentacyclic compound cyclotokinolide B was obtained from the natural phthalide tokinolide B under basic conditions, via the chemoselective g-enol lactone opening followed by a Michael addition of the generated carbanion to the enone and subsequent equilibration. This result confirms that some dimeric phthalides undergo intramolecular cyclizations in basic media.

📜 SIMILAR VOLUMES

Base-catalyzed intramolecular condensati
Base-catalyzed intramolecular condensations of diligustilide
✍ María Yolanda Rios; Guillermo Delgado; Georgina Espinosa-Pérez 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 227 KB

Treatment of diligustilide (I) with base afforded the pentacyclic compounds 2 -4 with novel carbon-carbon connectivities via lactone-ring opening, intramolecutar condensations and competitive equilibrations. This reaction provides a useful entry to modified dimeric phthalides.