Basiliolides were isolated from Thapsia garganica L. in 2005 and showed to be a potent inhibitor towards sacroendoplasmic reticulum Ca2+-ATPase (SERCA). Unlike thapsigargin, the basiliolides were found to be noncytotoxic, suggesting a reversible binding mechanism towards SERCA. Recently, we have successfully finished the total synthesis of (�)-basiliolide B via a biomimetic approach, which involved a 2-pyrone Diels-Alder cycloaddition for construction of the decalin framework (AB ring system) with the bridging lactone (D ring) and an intramolecular O-acylation cyclization for establishing the unprecedented 7-methoxy-4,5-dihydro-3H-oxepin-2-one moiety (C-ring). Moreover, we have developed a cyclopropanation/cyclopropane ring-opening strategy for diastereoselective installation of the stereogenic center at C8.

Biomimetic synthesis of (�)-basiliolide B

248th National Meeting (2014)

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