Consecutive Ireland–Claisen Enyne-Metathesis Strategy Enables Rapid Assembly of Cyclic Imine Core Cyclohexene Motif.

Autor: Lee, Hye Joon, Gladfelder, Joshua, Kandiyal, Priya, Zakarian, Armen
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Zdroj: Synlett; Aug2024, Vol. 35 Issue 13, p1540-1544, 5p
Abstrakt: An 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. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index