A Conia‐Ene‐Type Cyclization under Basic Conditions Enables an Efficient Synthesis of (−)‐Lycoposerramine R. Issue 3 (21st December 2016)

• Record Type: Journal Article
• Authors: Hartrampf, Felix W. W.; Furukawa, Takayuki; Trauner, Dirk
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 3(2017)
• Page Start: 893
• Page End: 896
• Publication Date: 2016-12-21
• Subjects: alkynes -- Conia-ene reaction -- hydrindanes -- lycopodium alkaloids -- total synthesis; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201610021
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: An enantioselective total synthesis of the Lycopodium alkaloid lycoposerramine R is presented. It relies on a base‐mediated cyclization that resembles the Conia‐ene reaction of ynones and gold‐catalyzed variants thereof. Thus, hydrindanones and other functionalized ring systems bearing an exocyclic alkene can be rapidly accessed at room temperature without noble metal catalysis or substrate preactivation. Abstract : An enantioselective total synthesis of the Lycopodium alkaloid lycoposerramine R relies on a base‐mediated cyclization that resembles the Conia‐ene reaction of ynones and gold‐catalyzed variants thereof. Thus, hydrindanones and other functionalized ring systems bearing an exo ‐methylene group can be rapidly accessed at room temperature without noble metal catalysis or substrate preactivation.