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A series of intramolecular condensation products were obtained by base-catalyzed treatment of the natural bioactive dimeric phthalide diligustilide (1) using different reaction conditions and the yields remarkably depend on these. The reaction conditions to obtain selectively the intramolecular condensation derivatives or the hydrolysis products of diligustilide (1) are described.
The novel pentacyclic compound cyclotokinolide B was obtained from the natural phthalide tokinolide B under basic conditions, via the chemoselective γ-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.
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