This 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.
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Communication
Enantioselective Total Synthesis of the Melodinus Alkaloid (+)-Meloscine†
Article first published online: 27 MAY 2008
DOI: 10.1002/anie.200800693
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Selig, P. and Bach, T. (2008), Enantioselective Total Synthesis of the Melodinus Alkaloid (+)-Meloscine. Angew. Chem. Int. Ed., 47: 5082–5084. doi: 10.1002/anie.200800693
- †
Publication History
- Issue published online: 16 JUN 2008
- Article first published online: 27 MAY 2008
- Manuscript Received: 12 FEB 2008
Funded by
- Deutsche Forschungsgemeinschaft. Grant Number: Ba 1372-10
- Fonds der Chemischen Industrie
Keywords:
- asymmetric synthesis;
- natural products;
- photochemistry;
- rearrangement;
- total synthesis
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).