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Total Synthesis of (±)-Strychnine via a [4 + 2]-Cycloaddition/Rearrangement Cascade

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journal contribution
posted on 18.01.2007, 00:00 by Hongjun Zhang, Jutatip Boonsombat, Albert Padwa
A new strategy for the synthesis of the Strychnos alkaloid (±)-strychnine has been developed and is based on an intramolecular [4 + 2]-cycloaddition/rearrangement cascade of an indolyl-substituted amidofuran. The critical D-ring was assembled by an intramolecular palladium-catalyzed enolate-driven cross-coupling of an N-tethered vinyl iodide.