A 11-Steps Total Synthesis of Magellanine through a Gold(I)-Catalyzed Dehydro Diels-Alder Reaction

Philippe McGee; Geneviève Bétournay; Francis Barabé; Louis Barriault

doi:10.1002/anie.201611606

A 11-Steps Total Synthesis of Magellanine through a Gold(I)-Catalyzed Dehydro Diels-Alder Reaction

Angew Chem Int Ed Engl. 2017 May 22;56(22):6280-6283. doi: 10.1002/anie.201611606. Epub 2017 Jan 12.

Authors

Philippe McGee¹, Geneviève Bétournay¹, Francis Barabé¹, Louis Barriault¹

Affiliation

¹ Center for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie-Curie, Ottawa, K1N 6N5, Canada.

PMID: 28079949
DOI: 10.1002/anie.201611606

Abstract

We have developed an innovative strategy for the formation of angular carbocycles via a gold(I)-catalyzed dehydro Diels-Alder reaction. This transformation provides rapid access to a variety of complex angular cores in excellent diastereoselectivities and high yields. The usefulness of this Au^I -catalyzed cycloaddition was further demonstrated by accomplishing a 11-steps total synthesis of (±)-magellanine.

Keywords: Diels-Alder reaction; gold; homogeneous catalysis; magellanine; total synthesis.

Publication types

Research Support, Non-U.S. Gov't