Abstract
AbstractAn efficient strategy for rapid assembly of the complex substituted cyclohexene core that is present in several cyclic imine marine toxins is presented. Several of these toxins, including pinnatoxin A and recently discovered portimine A, have been the focus of much attention due to their fascinating biological activities. We demonstrate that the substituted cyclohexene-diene motif, which is a challenging feature to access synthetically, can be prepared through a stepwise Ireland–Claisen rearrangement/enyne metathesis procedure beginning from chiral esters. This approach enables a divergent strategy that can be implemented in syntheses of cyclic imines or derivatives thereof.
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