The basiliolides and thapsigargin were both isolated from Thapsia garganica L. and exhibited similar levels of inhibitory potency towards sacroendoplasmic reticulum Ca2+-ATPase (SERCA) despite of their structure diversity. Unlike thapsigargin, the basiliolides were found to be noncytotoxic, suggesting a reversible binding mechanism towards SERCA. Since the basiliolides are noncytotoxic and are able to mobilize Ca2+ by targeting the ER, this class of natural products may found potential application for the treatment of neurodegenerative diseases. Our approach to basiliolide B (1) involved an intramolecular base-catalyzed reaction of 2H-Pyran-3,5-dione 3. The details of the development of the base-catalyzed Diels-Alder reactions and further progress towards the total synthesis of the target will be presented.

Base-catalyzed Diels-Alder approach towards basiliolide B

239th National Meeting (2010)

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