Formal Alder-ene reaction of a bicyclo[1.1.0]butane in the synthesis of the tricyclic quaternary ammonium core of daphniglaucins

Masafumi Ueda; Maciej A A Walczak; Peter Wipf

doi:10.1016/j.tetlet.2008.07.179

Formal Alder-ene reaction of a bicyclo[1.1.0]butane in the synthesis of the tricyclic quaternary ammonium core of daphniglaucins

Tetrahedron Lett. 2008 Jun;49(41):5986-5989. doi: 10.1016/j.tetlet.2008.07.179.

Authors

Masafumi Ueda¹, Maciej A A Walczak, Peter Wipf

Affiliation

¹ Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.

Abstract

A tricyclic substructure of the tetracyclic nitrogen core of the daphniglaucins was formed by an oxidative activation of the allyl side chain of a bicyclo[1.1.0]butylmethylamine, a spontaneous intramolecular formal Alder-ene reaction, and a selective cyclization of a triol intermediate.

Abstract

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