General Strategy for the Asymmetric Synthesis of the Picrotoxanes

摘要

The important role of picrotoxinin (1) as a GAB A antagonist has made it an invaluable tool for neurophysiology. It is representative of a growing family of compounds represented by corianin (2), asteromurin A (3), coriamyrtin (4), tutin (5), and thenovel structurally related picrodendrins, some of which show very similar biological functions. The high potency of these compounds, the unusual peutacyclic structure, and the high density of functionality have made them challenging targets for synthesis. In this communication, we develop a general strategy that provides flexibility to approach a number of members of this family. This strategy evolved from developments in metal-catalyzed Alder ene type reactions.