Enantioselective Total Synthesis of the Melodinus Alkaloid (+)-Meloscine†
Philipp Selig
Department of Chemistry, Technische Universität München, Lichtenbergstrasse 4, 85747 Garching (Germany), Fax: (+49) 89-2891-3315
Search for more papers by this authorThorsten Bach Prof. Dr.
Department of Chemistry, Technische Universität München, Lichtenbergstrasse 4, 85747 Garching (Germany), Fax: (+49) 89-2891-3315
Search for more papers by this authorPhilipp Selig
Department of Chemistry, Technische Universität München, Lichtenbergstrasse 4, 85747 Garching (Germany), Fax: (+49) 89-2891-3315
Search for more papers by this authorThorsten Bach Prof. Dr.
Department of Chemistry, Technische Universität München, Lichtenbergstrasse 4, 85747 Garching (Germany), Fax: (+49) 89-2891-3315
Search for more papers by this authorThis project was supported by the Deutsche Forschungsgemeinschaft as part of the Schwerpunktprogramm Organokatalyse (Ba 1372-10), by the Studienstiftung des Deutschen Volkes (doctoral fellowship to P.S.), and by the Fonds der Chemischen Industrie.
Graphical Abstract
Enantioselective synthesis in a new light: The template-controlled [2+2] photocycloaddition leading to product 1 is the first example of this type of reaction in natural product synthesis. In addition, a retro-benzilic acid rearrangement (→2), a Claisen rearrangement (→3), and a ring-closing metathesis played decisive roles in the synthesis of the alkaloid (+)-meloscine (4).
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