A 11‐Steps Total Synthesis of Magellanine through a Gold(I)‐Catalyzed Dehydro Diels–Alder Reaction. Issue 22 (12th January 2017)

• Record Type: Journal Article
• Authors: McGee, Philippe; Bétournay, Geneviève; Barabé, Francis; Barriault, Louis
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 22(2017)
• Page Start: 6280
• Page End: 6283
• Publication Date: 2017-01-12
• Subjects: Diels–Alder reaction -- gold -- homogeneous catalysis -- magellanine -- total synthesis; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201611606
• Languages: English
• ISSNs: 1433-7851

Abstract

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. Abstract : 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.