A Rapid and Stereocontrolled Synthesis of the Zizaane Ring System by Using an Intramolecular (4+3) Cycloaddition Reaction

Abstract

We report herein a very short synthetic approach to the tricyclo[6.2.1.0^1,5]undecane scaffold through a convergent and stereocontrolled route by using an intramolecular (4+3) cycloaddition of a simple furfuryl alcohol precursor with a pendant cyclopentadiene moiety. The formation of alternative reaction products under various conditions is also discussed.

Key words

cycloaddition - carbocation - furans - fused-ring systems - natural products

• References

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