3 years ago

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

A 11-Steps Total Synthesis of Magellanine through a Gold(I)-Catalyzed Dehydro Diels–Alder Reaction
Geneviève Bétournay, Philippe McGee, Francis Barabé, Louis Barriault
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 AuI-catalyzed cycloaddition was further demonstrated by accomplishing a 11-steps total synthesis of (±)-magellanine. Building complexity: An efficient and operationally simple method for the formation of angular carbocycles via a gold(I)-catalyzed dehydro Diels–Alder reaction is described. This transformation provides rapid access to complex angular cores in excellent diastereoselectivities. Its usefulness was further demonstrated by accomplishing a 11-steps total synthesis of (±)-magellanine.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201611606

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