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Reidispongiolide A is a representative member of the sphinxolide/reidispongiolide group of cytotoxic 26-membered macrolides of marine origin. By interacting with actin in the cell cytoskeleton, the reidispongiolides and sphinxolides are potent microfilament destabilizing agents that represent a promising mechanism of action for developing novel anticancer drugs. An aldol-based synthesis of a library of diastereomers of C(8)-C(16) and C(5)-C(16) fragments and detailed NMR comparison with a reported degradation fragment enabled a configurational assignment for a major part of the reidispongiolide macrocyclic core, thus setting a solid foundation for ongoing synthetic efforts.

proceedings of the national academy of sciences of the united states of america

Synthesis of antimicrofilament marine macrolides: Synthesis and configurational assignment of a C <sub>5</sub> –C <sub>16</sub> degradation fragment of reidispongiolide A

Synthesis of antimicrofilament marine macrolides: Synthesis and configurational assignment of a C 5 –C 16 degradation fragment of reidispongiolide A

Synthesis of antimicrofilament marine macrolides: Synthesis and configurational assignment of a C ₅ –C ₁₆ degradation fragment of reidispongiolide A